NPASS Compound

Structure

CID248775 OpenBabel06191716052D 35 35 0 0 1 0 0 0 0 0999 V2000 11.2583 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 17.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 15.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 4.3301 6.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 2 1 0 0 0 0 2 3 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 22 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 28 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 22 29 1 1 0 0 0 23 30 1 6 0 0 0 24 31 1 6 0 0 0 25 32 1 6 0 0 0 26 27 1 0 0 0 0 26 33 1 1 0 0 0 27 21 1 1 0 0 0 27 35 1 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.37
Volume:	540.546
LogP:	4.606
LogD:	3.47
LogS:	-5.036
# Rotatable Bonds:	22
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	4.16
Fsp3:	0.929
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:	-5.082
MDCK Permeability:	2.3420208890456706e-05
Pgp-inhibitor:	0.403
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.066
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	95.72151947021484%
Volume Distribution (VD):	1.03
Pgp-substrate:	2.6256604194641113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.334
CYP2C9-substrate:	0.714
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.366
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	10.589
Half-life (T1/2):	0.779

ADMET: Toxicity

hERG Blockers:	0.134
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.953
Carcinogencity:	0.418
Eye Corrosion:	0.094
Eye Irritation:	0.191
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC248775

Natural Product ID:	NPC248775
*Common Name:**	Cryptocaryol E
IUPAC Name:	(2S,3S)-3-hydroxy-2-[(2S,4S,6S,8R)-2,4,6,8-tetrahydroxytricosyl]-2,3-dihydropyran-6-one
Synonyms:	Cryptocaryol E
Standard InCHIKey:	CVJWXRNBYKUGQI-AIFRIFMOSA-N
Standard InCHI:	InChI=1S/C28H52O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22(29)18-23(30)19-24(31)20-25(32)21-27-26(33)16-17-28(34)35-27/h16-17,22-27,29-33H,2-15,18-21H2,1H3/t22-,23+,24+,25+,26+,27+/m1/s1
SMILES:	CCCCCCCCCCCCCCC[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:	CHEMBL1784376
PubChem CID:	54585961
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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	=	1800.0	nM	PMID[499336]

☑ 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 NPC248775 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	181
0.1-0.2	1807
0.2-0.3	5630
0.3-0.4	15272
0.4-0.5	12286
0.5-0.6	5167
0.6-0.7	1849
0.7-0.8	447
0.8-0.85	29
0.85-0.9	15
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC180725
0.9863	High Similarity	NPC470148
0.9863	High Similarity	NPC470149
0.973	High Similarity	NPC470147
0.973	High Similarity	NPC133226
0.9589	High Similarity	NPC474026
0.9306	High Similarity	NPC185186
0.9306	High Similarity	NPC327383
0.9079	High Similarity	NPC1180
0.9067	High Similarity	NPC475711
0.9054	High Similarity	NPC327041
0.9054	High Similarity	NPC285840
0.8904	High Similarity	NPC475762
0.8816	High Similarity	NPC233071
0.8784	High Similarity	NPC329914
0.8784	High Similarity	NPC329890
0.8765	High Similarity	NPC208473
0.8684	High Similarity	NPC188860
0.8608	High Similarity	NPC469469
0.859	High Similarity	NPC139712
0.8571	High Similarity	NPC3952
0.8519	High Similarity	NPC473308
0.8514	High Similarity	NPC476012
0.8514	High Similarity	NPC476037
0.8493	Intermediate Similarity	NPC475760
0.8472	Intermediate Similarity	NPC201356
0.8452	Intermediate Similarity	NPC133450
0.8395	Intermediate Similarity	NPC142111
0.8395	Intermediate Similarity	NPC473315
0.8353	Intermediate Similarity	NPC177668
0.8333	Intermediate Similarity	NPC19769
0.8333	Intermediate Similarity	NPC96414
0.8272	Intermediate Similarity	NPC251026
0.8205	Intermediate Similarity	NPC326661
0.8193	Intermediate Similarity	NPC471494
0.8125	Intermediate Similarity	NPC473947
0.8095	Intermediate Similarity	NPC311163
0.8095	Intermediate Similarity	NPC47937
0.8072	Intermediate Similarity	NPC160517
0.8072	Intermediate Similarity	NPC78673
0.8072	Intermediate Similarity	NPC186155
0.8068	Intermediate Similarity	NPC256368
0.8	Intermediate Similarity	NPC477314
0.7976	Intermediate Similarity	NPC182383
0.7976	Intermediate Similarity	NPC471567
0.7976	Intermediate Similarity	NPC322529
0.7976	Intermediate Similarity	NPC120398
0.7973	Intermediate Similarity	NPC276299
0.7973	Intermediate Similarity	NPC146811
0.7955	Intermediate Similarity	NPC238090
0.7955	Intermediate Similarity	NPC472195
0.7955	Intermediate Similarity	NPC472196
0.7945	Intermediate Similarity	NPC148233
0.7945	Intermediate Similarity	NPC25747
0.7931	Intermediate Similarity	NPC473311
0.7927	Intermediate Similarity	NPC8538
0.7927	Intermediate Similarity	NPC315731
0.7927	Intermediate Similarity	NPC184208
0.7917	Intermediate Similarity	NPC26810
0.7907	Intermediate Similarity	NPC40376
0.7907	Intermediate Similarity	NPC470137
0.7907	Intermediate Similarity	NPC21208
0.7907	Intermediate Similarity	NPC233551
0.7907	Intermediate Similarity	NPC20339
0.7907	Intermediate Similarity	NPC48338
0.7907	Intermediate Similarity	NPC280621
0.7882	Intermediate Similarity	NPC142117
0.7882	Intermediate Similarity	NPC69082
0.7882	Intermediate Similarity	NPC279267
0.7882	Intermediate Similarity	NPC61527
0.7882	Intermediate Similarity	NPC475581
0.7882	Intermediate Similarity	NPC240695
0.7882	Intermediate Similarity	NPC231096
0.7882	Intermediate Similarity	NPC114694
0.7882	Intermediate Similarity	NPC171174
0.7882	Intermediate Similarity	NPC107717
0.7882	Intermediate Similarity	NPC232555
0.7882	Intermediate Similarity	NPC62118
0.7865	Intermediate Similarity	NPC159698
0.7857	Intermediate Similarity	NPC163093
0.7857	Intermediate Similarity	NPC475035
0.7857	Intermediate Similarity	NPC266718
0.7857	Intermediate Similarity	NPC474251
0.7857	Intermediate Similarity	NPC156804
0.7821	Intermediate Similarity	NPC477085
0.7821	Intermediate Similarity	NPC470435
0.7802	Intermediate Similarity	NPC475332
0.7791	Intermediate Similarity	NPC178215
0.7778	Intermediate Similarity	NPC26223
0.7765	Intermediate Similarity	NPC110710
0.7765	Intermediate Similarity	NPC107986
0.7765	Intermediate Similarity	NPC470124
0.7765	Intermediate Similarity	NPC477013
0.7765	Intermediate Similarity	NPC223871
0.7765	Intermediate Similarity	NPC477014
0.7765	Intermediate Similarity	NPC231009
0.7765	Intermediate Similarity	NPC132496
0.7765	Intermediate Similarity	NPC1083
0.7765	Intermediate Similarity	NPC66346
0.7765	Intermediate Similarity	NPC286338
0.7765	Intermediate Similarity	NPC82795
0.7765	Intermediate Similarity	NPC473651
0.7765	Intermediate Similarity	NPC329615
0.7765	Intermediate Similarity	NPC473669
0.7765	Intermediate Similarity	NPC473478
0.7765	Intermediate Similarity	NPC103284
0.7765	Intermediate Similarity	NPC283085
0.7765	Intermediate Similarity	NPC329838
0.7763	Intermediate Similarity	NPC63873
0.7738	Intermediate Similarity	NPC44261
0.7738	Intermediate Similarity	NPC253801
0.7733	Intermediate Similarity	NPC124586
0.7727	Intermediate Similarity	NPC239517
0.7727	Intermediate Similarity	NPC473904
0.7722	Intermediate Similarity	NPC315843
0.7722	Intermediate Similarity	NPC107654
0.7711	Intermediate Similarity	NPC297440
0.7703	Intermediate Similarity	NPC308457
0.7701	Intermediate Similarity	NPC473905
0.7701	Intermediate Similarity	NPC169511
0.7701	Intermediate Similarity	NPC89001
0.7701	Intermediate Similarity	NPC172821
0.7701	Intermediate Similarity	NPC61257
0.7701	Intermediate Similarity	NPC261952
0.7701	Intermediate Similarity	NPC151403
0.7701	Intermediate Similarity	NPC320458
0.7701	Intermediate Similarity	NPC39754
0.7701	Intermediate Similarity	NPC171135
0.7701	Intermediate Similarity	NPC191929
0.7701	Intermediate Similarity	NPC274446
0.7701	Intermediate Similarity	NPC242364
0.7701	Intermediate Similarity	NPC81045
0.7701	Intermediate Similarity	NPC320569
0.7701	Intermediate Similarity	NPC100454
0.7701	Intermediate Similarity	NPC133730
0.7701	Intermediate Similarity	NPC287164
0.7701	Intermediate Similarity	NPC234077
0.7692	Intermediate Similarity	NPC472995
0.7692	Intermediate Similarity	NPC477087
0.7692	Intermediate Similarity	NPC477086
0.7683	Intermediate Similarity	NPC86971
0.7683	Intermediate Similarity	NPC55304
0.7683	Intermediate Similarity	NPC226226
0.7674	Intermediate Similarity	NPC308412
0.7674	Intermediate Similarity	NPC293136
0.7674	Intermediate Similarity	NPC210218
0.7674	Intermediate Similarity	NPC204686
0.7674	Intermediate Similarity	NPC477015
0.7674	Intermediate Similarity	NPC103523
0.7674	Intermediate Similarity	NPC473687
0.7674	Intermediate Similarity	NPC132940
0.7674	Intermediate Similarity	NPC134865
0.7674	Intermediate Similarity	NPC134885
0.7674	Intermediate Similarity	NPC219498
0.7674	Intermediate Similarity	NPC112685
0.7674	Intermediate Similarity	NPC134807
0.7674	Intermediate Similarity	NPC309211
0.7674	Intermediate Similarity	NPC241360
0.7667	Intermediate Similarity	NPC469491
0.7662	Intermediate Similarity	NPC475982
0.7654	Intermediate Similarity	NPC477203
0.764	Intermediate Similarity	NPC469410
0.7639	Intermediate Similarity	NPC302564
0.7639	Intermediate Similarity	NPC22897
0.7639	Intermediate Similarity	NPC159650
0.7625	Intermediate Similarity	NPC260396
0.7619	Intermediate Similarity	NPC180363
0.7619	Intermediate Similarity	NPC473780
0.7619	Intermediate Similarity	NPC11332
0.7619	Intermediate Similarity	NPC73310
0.7619	Intermediate Similarity	NPC475159
0.7619	Intermediate Similarity	NPC329829
0.7619	Intermediate Similarity	NPC473712
0.7619	Intermediate Similarity	NPC473529
0.7619	Intermediate Similarity	NPC65930
0.7619	Intermediate Similarity	NPC131002
0.7619	Intermediate Similarity	NPC94875
0.7619	Intermediate Similarity	NPC145914
0.7614	Intermediate Similarity	NPC42598
0.7614	Intermediate Similarity	NPC40066
0.7614	Intermediate Similarity	NPC477011
0.7614	Intermediate Similarity	NPC20621
0.7614	Intermediate Similarity	NPC93794
0.7614	Intermediate Similarity	NPC139418
0.7614	Intermediate Similarity	NPC477016
0.7614	Intermediate Similarity	NPC318963
0.7614	Intermediate Similarity	NPC477017
0.7614	Intermediate Similarity	NPC81778
0.7614	Intermediate Similarity	NPC473504
0.7614	Intermediate Similarity	NPC91067
0.7609	Intermediate Similarity	NPC40812
0.76	Intermediate Similarity	NPC273600
0.7595	Intermediate Similarity	NPC284006
0.7586	Intermediate Similarity	NPC199382
0.7586	Intermediate Similarity	NPC313658
0.7586	Intermediate Similarity	NPC316138
0.7586	Intermediate Similarity	NPC258068
0.7586	Intermediate Similarity	NPC476583
0.7586	Intermediate Similarity	NPC475186
0.7586	Intermediate Similarity	NPC473995

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 NPC248775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	2432
0.2-0.3	3726
0.3-0.4	2135
0.4-0.5	532
0.5-0.6	140
0.6-0.7	34
0.7-0.8	2
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
0.7931	Intermediate Similarity	NPD7838	Discovery
0.7727	Intermediate Similarity	NPD46	Approved
0.7727	Intermediate Similarity	NPD6698	Approved
0.7553	Intermediate Similarity	NPD5344	Discontinued
0.734	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6648	Approved
0.7065	Intermediate Similarity	NPD7983	Approved
0.6854	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4251	Approved
0.6813	Remote Similarity	NPD4250	Approved
0.6782	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4249	Approved
0.6635	Remote Similarity	NPD6371	Approved
0.6633	Remote Similarity	NPD4225	Approved
0.6623	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6686	Approved
0.6582	Remote Similarity	NPD3197	Phase 1
0.6579	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4271	Approved
0.6552	Remote Similarity	NPD4268	Approved
0.6505	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5785	Approved
0.6421	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4819	Approved
0.6404	Remote Similarity	NPD4820	Approved
0.6404	Remote Similarity	NPD4821	Approved
0.6404	Remote Similarity	NPD4822	Approved
0.6374	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD9119	Approved
0.6364	Remote Similarity	NPD6109	Phase 1
0.6364	Remote Similarity	NPD69	Approved
0.6296	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5778	Approved
0.6289	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD4756	Discovery
0.6238	Remote Similarity	NPD7640	Approved
0.6238	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD5363	Approved
0.6234	Remote Similarity	NPD9118	Approved
0.6196	Remote Similarity	NPD6110	Phase 1
0.6195	Remote Similarity	NPD7503	Approved
0.6186	Remote Similarity	NPD7637	Suspended
0.6139	Remote Similarity	NPD7638	Approved
0.6126	Remote Similarity	NPD7115	Discovery
0.61	Remote Similarity	NPD7839	Suspended
0.6087	Remote Similarity	NPD7830	Approved
0.6087	Remote Similarity	NPD7829	Approved
0.6064	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6053	Discontinued
0.6053	Remote Similarity	NPD8513	Phase 3
0.6022	Remote Similarity	NPD5362	Discontinued
0.6019	Remote Similarity	NPD6421	Discontinued
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7505	Discontinued
0.5948	Remote Similarity	NPD7642	Approved
0.5938	Remote Similarity	NPD7524	Approved
0.5929	Remote Similarity	NPD7328	Approved
0.5929	Remote Similarity	NPD7327	Approved
0.5914	Remote Similarity	NPD4270	Approved
0.5914	Remote Similarity	NPD6435	Approved
0.5914	Remote Similarity	NPD4269	Approved
0.5913	Remote Similarity	NPD8516	Approved
0.5913	Remote Similarity	NPD8517	Approved
0.5913	Remote Similarity	NPD8515	Approved
0.5913	Remote Similarity	NPD8033	Approved
0.5905	Remote Similarity	NPD1407	Approved
0.5877	Remote Similarity	NPD7516	Approved
0.587	Remote Similarity	NPD4252	Approved
0.5851	Remote Similarity	NPD5332	Approved
0.5851	Remote Similarity	NPD5331	Approved
0.5844	Remote Similarity	NPD3196	Approved
0.5844	Remote Similarity	NPD3728	Approved
0.5844	Remote Similarity	NPD4266	Approved
0.5844	Remote Similarity	NPD3730	Approved
0.5844	Remote Similarity	NPD3195	Phase 2
0.5844	Remote Similarity	NPD3194	Approved
0.5833	Remote Similarity	NPD5786	Approved
0.5826	Remote Similarity	NPD8377	Approved
0.5826	Remote Similarity	NPD8294	Approved
0.5824	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4790	Discontinued
0.5789	Remote Similarity	NPD7641	Discontinued
0.5789	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.578	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD8378	Approved
0.5776	Remote Similarity	NPD8380	Approved
0.5776	Remote Similarity	NPD8296	Approved
0.5776	Remote Similarity	NPD8444	Approved
0.5776	Remote Similarity	NPD8379	Approved
0.5776	Remote Similarity	NPD8335	Approved
0.5745	Remote Similarity	NPD5209	Approved
0.5714	Remote Similarity	NPD8273	Phase 1
0.5714	Remote Similarity	NPD3172	Approved
0.5702	Remote Similarity	NPD7500	Approved
0.57	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD5368	Approved
0.5684	Remote Similarity	NPD6695	Phase 3
0.5676	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8074	Phase 3
0.5667	Remote Similarity	NPD8039	Approved
0.566	Remote Similarity	NPD7632	Discontinued
0.5658	Remote Similarity	NPD6927	Phase 3
0.5657	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6101	Approved
0.5657	Remote Similarity	NPD1695	Approved
0.5657	Remote Similarity	NPD5370	Suspended
0.5648	Remote Similarity	NPD4211	Phase 1
0.5638	Remote Similarity	NPD5369	Approved
0.5618	Remote Similarity	NPD4732	Discontinued
0.5607	Remote Similarity	NPD6647	Phase 2

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