NPASS Compound

Structure

NPC285840 OpenBabel07101719142D 40 40 0 0 1 0 0 0 0 0999 V2000 -15.5885 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 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 -9.5263 0.5000 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 -8.6603 -0.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 -10.3923 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -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 3 1 0 0 0 0 2 25 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 17 1 0 0 0 0 16 18 1 0 0 0 0 16 19 2 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 20 26 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 23 30 1 0 0 0 0 24 29 1 0 0 0 0 25 33 2 0 0 0 0 25 39 1 0 0 0 0 26 34 1 6 0 0 0 27 35 1 6 0 0 0 28 36 1 6 0 0 0 29 37 1 6 0 0 0 30 17 1 6 0 0 0 30 39 1 0 0 0 0 31 24 1 6 0 0 0 31 40 1 0 0 0 0 32 38 2 0 0 0 0 32 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.41
Volume:	615.884
LogP:	6.266
LogD:	3.707
LogS:	-5.763
# Rotatable Bonds:	26
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.063
Synthetic Accessibility Score:	4.537
Fsp3:	0.875
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:	-5.077
MDCK Permeability:	3.591322820284404e-05
Pgp-inhibitor:	0.312
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	96.75878143310547%
Volume Distribution (VD):	1.384
Pgp-substrate:	3.551647186279297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.601
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	7.543
Half-life (T1/2):	0.492

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.731
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.981
Carcinogencity:	0.258
Eye Corrosion:	0.76
Eye Irritation:	0.337
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC285840

Natural Product ID:	NPC285840
*Common Name:**	Cryptocaryol B
IUPAC Name:	[(2S,4S,6R,8R,10R)-2,4,6,8-tetrahydroxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]pentacosan-10-yl] acetate
Synonyms:	Cryptocaryol B
Standard InCHIKey:	JUDSGWKIMNPKNH-ZAKLOLAYSA-N
Standard InCHI:	InChI=1S/C32H58O8/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17-30(39-25(2)33)23-28(36)21-26(34)20-27(35)22-29(37)24-31-18-16-19-32(38)40-31/h16,19,26-31,34-37H,3-15,17-18,20-24H2,1-2H3/t26-,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]1CC=CC(=O)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784373
PubChem CID:	54582082
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]

☑ 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	=	3000.0	nM	PMID[509964]

☑ 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 NPC285840 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	171
0.1-0.2	1776
0.2-0.3	6203
0.3-0.4	17204
0.4-0.5	10594
0.5-0.6	4843
0.6-0.7	1545
0.7-0.8	313
0.8-0.85	23
0.85-0.9	8
0.9-0.95	12
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC327041
0.971	High Similarity	NPC327383
0.971	High Similarity	NPC185186
0.9324	High Similarity	NPC133226
0.9324	High Similarity	NPC470147
0.9189	High Similarity	NPC470148
0.9189	High Similarity	NPC470149
0.9189	High Similarity	NPC180725
0.9178	High Similarity	NPC474026
0.9155	High Similarity	NPC329914
0.9054	High Similarity	NPC248775
0.8933	High Similarity	NPC139712
0.8889	High Similarity	NPC329890
0.8873	High Similarity	NPC476012
0.8784	High Similarity	NPC188860
0.875	High Similarity	NPC475762
0.8701	High Similarity	NPC8538
0.8701	High Similarity	NPC184208
0.8667	High Similarity	NPC233071
0.8611	High Similarity	NPC476037
0.8462	Intermediate Similarity	NPC315731
0.8421	Intermediate Similarity	NPC475711
0.8421	Intermediate Similarity	NPC477203
0.8333	Intermediate Similarity	NPC475760
0.8289	Intermediate Similarity	NPC469880
0.8289	Intermediate Similarity	NPC477202
0.8228	Intermediate Similarity	NPC469469
0.8205	Intermediate Similarity	NPC1180
0.8171	Intermediate Similarity	NPC208473
0.8118	Intermediate Similarity	NPC476084
0.8118	Intermediate Similarity	NPC206679
0.8118	Intermediate Similarity	NPC114172
0.8118	Intermediate Similarity	NPC471324
0.8118	Intermediate Similarity	NPC476075
0.8072	Intermediate Similarity	NPC199382
0.8056	Intermediate Similarity	NPC146811
0.8023	Intermediate Similarity	NPC159092
0.8023	Intermediate Similarity	NPC109406
0.8	Intermediate Similarity	NPC177668
0.7975	Intermediate Similarity	NPC473947
0.7971	Intermediate Similarity	NPC22897
0.7971	Intermediate Similarity	NPC159650
0.7952	Intermediate Similarity	NPC47220
0.7952	Intermediate Similarity	NPC186332
0.7927	Intermediate Similarity	NPC473308
0.7917	Intermediate Similarity	NPC96414
0.7901	Intermediate Similarity	NPC251026
0.7895	Intermediate Similarity	NPC477085
0.7882	Intermediate Similarity	NPC133450
0.7808	Intermediate Similarity	NPC201356
0.7805	Intermediate Similarity	NPC473315
0.7805	Intermediate Similarity	NPC142111
0.7792	Intermediate Similarity	NPC477204
0.7791	Intermediate Similarity	NPC3952
0.7778	Intermediate Similarity	NPC148233
0.7778	Intermediate Similarity	NPC25747
0.7765	Intermediate Similarity	NPC20339
0.7765	Intermediate Similarity	NPC280621
0.7765	Intermediate Similarity	NPC233551
0.7765	Intermediate Similarity	NPC48338
0.7765	Intermediate Similarity	NPC21208
0.7765	Intermediate Similarity	NPC40376
0.7763	Intermediate Similarity	NPC477087
0.7763	Intermediate Similarity	NPC477086
0.7763	Intermediate Similarity	NPC293114
0.7746	Intermediate Similarity	NPC26810
0.7738	Intermediate Similarity	NPC47937
0.7727	Intermediate Similarity	NPC256368
0.7711	Intermediate Similarity	NPC474251
0.7711	Intermediate Similarity	NPC186155
0.7711	Intermediate Similarity	NPC160517
0.7711	Intermediate Similarity	NPC78673
0.7692	Intermediate Similarity	NPC260396
0.7667	Intermediate Similarity	NPC475332
0.7662	Intermediate Similarity	NPC284006
0.7647	Intermediate Similarity	NPC178215
0.7647	Intermediate Similarity	NPC313658
0.7647	Intermediate Similarity	NPC316138
0.764	Intermediate Similarity	NPC300710
0.7625	Intermediate Similarity	NPC182292
0.7625	Intermediate Similarity	NPC477314
0.7619	Intermediate Similarity	NPC329615
0.7619	Intermediate Similarity	NPC477013
0.7619	Intermediate Similarity	NPC242233
0.7619	Intermediate Similarity	NPC182383
0.7619	Intermediate Similarity	NPC477014
0.7619	Intermediate Similarity	NPC120398
0.7619	Intermediate Similarity	NPC471494
0.7619	Intermediate Similarity	NPC471567
0.7619	Intermediate Similarity	NPC322529
0.7619	Intermediate Similarity	NPC329838
0.7614	Intermediate Similarity	NPC238090
0.7614	Intermediate Similarity	NPC472195
0.7614	Intermediate Similarity	NPC472196
0.7606	Intermediate Similarity	NPC154908
0.7606	Intermediate Similarity	NPC158368
0.7606	Intermediate Similarity	NPC226872
0.7606	Intermediate Similarity	NPC26223
0.7606	Intermediate Similarity	NPC252851
0.759	Intermediate Similarity	NPC253801
0.7586	Intermediate Similarity	NPC473311
0.7586	Intermediate Similarity	NPC239517
0.7568	Intermediate Similarity	NPC124586
0.7558	Intermediate Similarity	NPC470137
0.7558	Intermediate Similarity	NPC89001
0.7558	Intermediate Similarity	NPC473905
0.7558	Intermediate Similarity	NPC320458
0.7556	Intermediate Similarity	NPC288350
0.7556	Intermediate Similarity	NPC173329
0.7556	Intermediate Similarity	NPC255410
0.7534	Intermediate Similarity	NPC308457
0.7532	Intermediate Similarity	NPC316185
0.7531	Intermediate Similarity	NPC226226
0.7531	Intermediate Similarity	NPC55304
0.7529	Intermediate Similarity	NPC114694
0.7529	Intermediate Similarity	NPC219652
0.7529	Intermediate Similarity	NPC142117
0.7529	Intermediate Similarity	NPC475581
0.7529	Intermediate Similarity	NPC279267
0.7529	Intermediate Similarity	NPC25703
0.7529	Intermediate Similarity	NPC61527
0.7529	Intermediate Similarity	NPC240695
0.7529	Intermediate Similarity	NPC62118
0.7529	Intermediate Similarity	NPC69082
0.7529	Intermediate Similarity	NPC477015
0.7529	Intermediate Similarity	NPC309211
0.7529	Intermediate Similarity	NPC103523
0.7529	Intermediate Similarity	NPC282815
0.7529	Intermediate Similarity	NPC107717
0.7529	Intermediate Similarity	NPC232555
0.7529	Intermediate Similarity	NPC134865
0.7529	Intermediate Similarity	NPC231096
0.7529	Intermediate Similarity	NPC473840
0.7529	Intermediate Similarity	NPC171174
0.7528	Intermediate Similarity	NPC159698
0.75	Intermediate Similarity	NPC475004
0.75	Intermediate Similarity	NPC156804
0.75	Intermediate Similarity	NPC101622
0.75	Intermediate Similarity	NPC84360
0.75	Intermediate Similarity	NPC151481
0.75	Intermediate Similarity	NPC163093
0.7473	Intermediate Similarity	NPC120299
0.7471	Intermediate Similarity	NPC477017
0.7471	Intermediate Similarity	NPC42598
0.7471	Intermediate Similarity	NPC81778
0.7471	Intermediate Similarity	NPC477011
0.7471	Intermediate Similarity	NPC318963
0.7471	Intermediate Similarity	NPC473504
0.7471	Intermediate Similarity	NPC20621
0.7471	Intermediate Similarity	NPC91067
0.7471	Intermediate Similarity	NPC40066
0.7471	Intermediate Similarity	NPC93794
0.7471	Intermediate Similarity	NPC477016
0.747	Intermediate Similarity	NPC10080
0.747	Intermediate Similarity	NPC475159
0.747	Intermediate Similarity	NPC11332
0.747	Intermediate Similarity	NPC131002
0.747	Intermediate Similarity	NPC123908
0.747	Intermediate Similarity	NPC473712
0.747	Intermediate Similarity	NPC65930
0.747	Intermediate Similarity	NPC145914
0.747	Intermediate Similarity	NPC473780
0.747	Intermediate Similarity	NPC473529
0.747	Intermediate Similarity	NPC180363
0.747	Intermediate Similarity	NPC94875
0.747	Intermediate Similarity	NPC329829
0.747	Intermediate Similarity	NPC73310
0.7442	Intermediate Similarity	NPC473995
0.7442	Intermediate Similarity	NPC476583
0.7442	Intermediate Similarity	NPC20533
0.7442	Intermediate Similarity	NPC258068
0.7432	Intermediate Similarity	NPC282760
0.7432	Intermediate Similarity	NPC19769
0.7412	Intermediate Similarity	NPC82795
0.7412	Intermediate Similarity	NPC107986
0.7412	Intermediate Similarity	NPC473669
0.7412	Intermediate Similarity	NPC473478
0.7412	Intermediate Similarity	NPC283085
0.7412	Intermediate Similarity	NPC470124
0.7412	Intermediate Similarity	NPC1083
0.7412	Intermediate Similarity	NPC473671
0.7412	Intermediate Similarity	NPC223871
0.7412	Intermediate Similarity	NPC286338
0.7412	Intermediate Similarity	NPC66346
0.7412	Intermediate Similarity	NPC319036
0.7412	Intermediate Similarity	NPC475268
0.7412	Intermediate Similarity	NPC473156
0.7412	Intermediate Similarity	NPC39279
0.7412	Intermediate Similarity	NPC25764
0.7412	Intermediate Similarity	NPC231009
0.7412	Intermediate Similarity	NPC77871
0.7412	Intermediate Similarity	NPC477018
0.7412	Intermediate Similarity	NPC39167
0.7412	Intermediate Similarity	NPC202055
0.7412	Intermediate Similarity	NPC470400
0.7412	Intermediate Similarity	NPC235809
0.7412	Intermediate Similarity	NPC132496
0.7412	Intermediate Similarity	NPC9678
0.7412	Intermediate Similarity	NPC473651
0.7412	Intermediate Similarity	NPC100921

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 NPC285840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	2452
0.2-0.3	3830
0.3-0.4	2108
0.4-0.5	465
0.5-0.6	128
0.6-0.7	24
0.7-0.8	1
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
0.7791	Intermediate Similarity	NPD7838	Discovery
0.7386	Intermediate Similarity	NPD46	Approved
0.7386	Intermediate Similarity	NPD6698	Approved
0.7204	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5344	Discontinued
0.6795	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4251	Approved
0.6628	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6648	Approved
0.6556	Remote Similarity	NPD4249	Approved
0.6538	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7839	Suspended
0.6452	Remote Similarity	NPD5785	Approved
0.641	Remote Similarity	NPD3197	Phase 1
0.6404	Remote Similarity	NPD7154	Phase 3
0.6395	Remote Similarity	NPD4271	Approved
0.6395	Remote Similarity	NPD4268	Approved
0.6373	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7638	Approved
0.6316	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD5779	Approved
0.6311	Remote Similarity	NPD6686	Approved
0.6286	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4756	Discovery
0.6264	Remote Similarity	NPD5363	Approved
0.6263	Remote Similarity	NPD7639	Approved
0.6263	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD4819	Approved
0.6211	Remote Similarity	NPD7637	Suspended
0.6162	Remote Similarity	NPD4225	Approved
0.6105	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD3195	Phase 2
0.6081	Remote Similarity	NPD3194	Approved
0.6081	Remote Similarity	NPD3196	Approved
0.6081	Remote Similarity	NPD4266	Approved
0.6075	Remote Similarity	NPD6053	Discontinued
0.6047	Remote Similarity	NPD8039	Approved
0.6044	Remote Similarity	NPD5362	Discontinued
0.6038	Remote Similarity	NPD6371	Approved
0.602	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD6109	Phase 1
0.5965	Remote Similarity	NPD7829	Approved
0.5965	Remote Similarity	NPD7830	Approved
0.596	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD3172	Approved
0.5934	Remote Similarity	NPD4270	Approved
0.5934	Remote Similarity	NPD6435	Approved
0.5934	Remote Similarity	NPD5209	Approved
0.5934	Remote Similarity	NPD4269	Approved
0.5929	Remote Similarity	NPD7503	Approved
0.5914	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.589	Remote Similarity	NPD6927	Phase 3
0.5889	Remote Similarity	NPD4252	Approved
0.587	Remote Similarity	NPD5331	Approved
0.587	Remote Similarity	NPD5332	Approved
0.5851	Remote Similarity	NPD5786	Approved
0.5843	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6101	Approved
0.5824	Remote Similarity	NPD5369	Approved
0.5824	Remote Similarity	NPD4790	Discontinued
0.581	Remote Similarity	NPD4211	Phase 1
0.5802	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD8513	Phase 3
0.5789	Remote Similarity	NPD8033	Approved
0.5769	Remote Similarity	NPD9119	Approved
0.5769	Remote Similarity	NPD69	Approved
0.5761	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5368	Approved
0.5702	Remote Similarity	NPD8294	Approved
0.5702	Remote Similarity	NPD8377	Approved
0.5699	Remote Similarity	NPD6695	Phase 3
0.5699	Remote Similarity	NPD6110	Phase 1
0.5694	Remote Similarity	NPD5343	Approved
0.569	Remote Similarity	NPD7642	Approved
0.5679	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD29	Approved
0.5676	Remote Similarity	NPD28	Approved
0.5673	Remote Similarity	NPD7632	Discontinued
0.567	Remote Similarity	NPD1695	Approved
0.567	Remote Similarity	NPD5370	Suspended
0.5664	Remote Similarity	NPD7328	Approved
0.5664	Remote Similarity	NPD7327	Approved
0.5663	Remote Similarity	NPD3704	Approved
0.5663	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8444	Approved
0.5652	Remote Similarity	NPD8517	Approved
0.5652	Remote Similarity	NPD8378	Approved
0.5652	Remote Similarity	NPD8516	Approved
0.5652	Remote Similarity	NPD8380	Approved
0.5652	Remote Similarity	NPD8296	Approved
0.5652	Remote Similarity	NPD8379	Approved
0.5652	Remote Similarity	NPD8335	Approved
0.5652	Remote Similarity	NPD8515	Approved
0.5641	Remote Similarity	NPD9118	Approved
0.5638	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD39	Approved
0.5632	Remote Similarity	NPD4732	Discontinued
0.5625	Remote Similarity	NPD7750	Discontinued
0.5619	Remote Similarity	NPD6647	Phase 2
0.5616	Remote Similarity	NPD3173	Approved
0.5614	Remote Similarity	NPD7516	Approved
0.56	Remote Similarity	NPD5282	Discontinued

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