NPASS Compound

Structure

NPC8729 OpenBabel07101719132D 27 30 0 0 1 0 0 0 0 0999 V2000 2.3379 -0.0204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5369 2.2919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7896 -1.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5383 -1.3768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1510 -0.5758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2946 1.2767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7359 -0.5758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2549 -0.8534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4956 -0.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1793 -0.9214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7070 -0.3337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5369 0.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3271 -0.7865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0759 -2.1778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7359 -0.0204 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7070 0.2573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2549 0.2573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2260 -0.0204 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2549 0.8127 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2260 -0.5758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7668 0.5172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2549 -0.8891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5383 -2.9788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1711 -1.8102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3271 0.7101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1510 -2.1778 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 14 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 13 22 1 0 0 0 0 14 23 2 0 0 0 0 14 26 1 0 0 0 0 15 12 1 1 0 0 0 15 17 1 0 0 0 0 16 11 1 1 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	393.521
LogP:	3.657
LogD:	3.306
LogS:	-4.04
# Rotatable Bonds:	3
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	6.183
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.726
MDCK Permeability:	1.7002044842229225e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.327
Plasma Protein Binding (PPB):	75.49339294433594%
Volume Distribution (VD):	1.657
Pgp-substrate:	18.646236419677734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.723
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.518
CYP3A4-substrate:	0.87

ADMET: Excretion

Clearance (CL):	8.814
Half-life (T1/2):	0.396

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.561
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.117
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.114
Carcinogencity:	0.346
Eye Corrosion:	0.018
Eye Irritation:	0.095
Respiratory Toxicity:	0.17

Download Data

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

Natural Product: NPC8729

Natural Product ID:	NPC8729
*Common Name:**	Pachycladin E
IUPAC Name:	n.a.
Synonyms:	Pachycladin E
Standard InCHIKey:	KKHDVLLKJKRJGE-JTQPAYLFSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-12(2)15-7-8-20(5,26-14(4)23)18-16-11-13(3)22(24)10-9-21(6,27-22)19(25-16)17(15)18/h12,15-19,24H,3,7-11H2,1-2,4-6H3/t15-,16-,17-,18-,19-,20-,21-,22+/m1/s1
SMILES:	CC(C)[C@H]1CC[C@](C)([C@@H]2[C@H]3CC(=C)[C@@]4(CC[C@](C)([C@@H]([C@H]12)O3)O4)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095495
PubChem CID:	46833118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	red sea soft coral	n.a.	PMID[20420415]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	64000.0	nM	PMID[490681]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	15624999.06	nM	PMID[490681]

☑ 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 NPC8729 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	198
0.1-0.2	1760
0.2-0.3	5505
0.3-0.4	14240
0.4-0.5	9242
0.5-0.6	8007
0.6-0.7	3460
0.7-0.8	276
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC475684
0.8706	High Similarity	NPC76054
0.8652	High Similarity	NPC44538
0.8621	High Similarity	NPC127917
0.8556	High Similarity	NPC476723
0.8556	High Similarity	NPC476724
0.8556	High Similarity	NPC470260
0.8556	High Similarity	NPC75443
0.8556	High Similarity	NPC92370
0.8462	Intermediate Similarity	NPC291875
0.8462	Intermediate Similarity	NPC161560
0.8427	Intermediate Similarity	NPC196911
0.8427	Intermediate Similarity	NPC471379
0.8409	Intermediate Similarity	NPC5958
0.8295	Intermediate Similarity	NPC103171
0.828	Intermediate Similarity	NPC91251
0.828	Intermediate Similarity	NPC122057
0.8222	Intermediate Similarity	NPC476725
0.8211	Intermediate Similarity	NPC476720
0.8182	Intermediate Similarity	NPC77003
0.8172	Intermediate Similarity	NPC471378
0.8172	Intermediate Similarity	NPC312471
0.8085	Intermediate Similarity	NPC312805
0.8046	Intermediate Similarity	NPC264610
0.8039	Intermediate Similarity	NPC38948
0.7978	Intermediate Similarity	NPC118116
0.7961	Intermediate Similarity	NPC206618
0.7938	Intermediate Similarity	NPC284194
0.7938	Intermediate Similarity	NPC471765
0.7938	Intermediate Similarity	NPC211810
0.7938	Intermediate Similarity	NPC221801
0.7917	Intermediate Similarity	NPC472360
0.7917	Intermediate Similarity	NPC472416
0.7879	Intermediate Similarity	NPC272223
0.7857	Intermediate Similarity	NPC473244
0.7822	Intermediate Similarity	NPC120009
0.7802	Intermediate Similarity	NPC239308
0.7789	Intermediate Similarity	NPC220216
0.7742	Intermediate Similarity	NPC214315
0.7742	Intermediate Similarity	NPC321812
0.7742	Intermediate Similarity	NPC322922
0.7723	Intermediate Similarity	NPC177701
0.7723	Intermediate Similarity	NPC472815
0.7708	Intermediate Similarity	NPC124374
0.77	Intermediate Similarity	NPC188968
0.77	Intermediate Similarity	NPC38855
0.7692	Intermediate Similarity	NPC473517
0.7684	Intermediate Similarity	NPC246028
0.7684	Intermediate Similarity	NPC261320
0.7629	Intermediate Similarity	NPC99653
0.7624	Intermediate Similarity	NPC472554
0.7624	Intermediate Similarity	NPC144486
0.7619	Intermediate Similarity	NPC473570
0.76	Intermediate Similarity	NPC469725
0.7596	Intermediate Similarity	NPC471205
0.7596	Intermediate Similarity	NPC472390
0.7576	Intermediate Similarity	NPC473964
0.7576	Intermediate Similarity	NPC284518
0.7576	Intermediate Similarity	NPC129569
0.7573	Intermediate Similarity	NPC473543
0.7551	Intermediate Similarity	NPC105375
0.7551	Intermediate Similarity	NPC96736
0.7551	Intermediate Similarity	NPC178949
0.7551	Intermediate Similarity	NPC182826
0.7551	Intermediate Similarity	NPC3359
0.7549	Intermediate Similarity	NPC31085
0.7549	Intermediate Similarity	NPC238397
0.7549	Intermediate Similarity	NPC472552
0.7549	Intermediate Similarity	NPC471363
0.7527	Intermediate Similarity	NPC18953
0.7526	Intermediate Similarity	NPC130840
0.7525	Intermediate Similarity	NPC477972
0.7525	Intermediate Similarity	NPC228251
0.7525	Intermediate Similarity	NPC477968
0.7525	Intermediate Similarity	NPC219285
0.7525	Intermediate Similarity	NPC161527
0.7525	Intermediate Similarity	NPC477971
0.7525	Intermediate Similarity	NPC324841
0.7525	Intermediate Similarity	NPC20113
0.7524	Intermediate Similarity	NPC217921
0.7524	Intermediate Similarity	NPC135015
0.7524	Intermediate Similarity	NPC128795
0.7524	Intermediate Similarity	NPC48548
0.75	Intermediate Similarity	NPC97867
0.75	Intermediate Similarity	NPC254121
0.75	Intermediate Similarity	NPC472998
0.75	Intermediate Similarity	NPC111348
0.75	Intermediate Similarity	NPC274793
0.75	Intermediate Similarity	NPC51719
0.75	Intermediate Similarity	NPC36479
0.75	Intermediate Similarity	NPC470055
0.75	Intermediate Similarity	NPC470056
0.75	Intermediate Similarity	NPC473963
0.7477	Intermediate Similarity	NPC17791
0.7476	Intermediate Similarity	NPC471467
0.7476	Intermediate Similarity	NPC7613
0.7476	Intermediate Similarity	NPC134270
0.7476	Intermediate Similarity	NPC475889
0.7476	Intermediate Similarity	NPC99510
0.7476	Intermediate Similarity	NPC127933
0.7476	Intermediate Similarity	NPC7644
0.7476	Intermediate Similarity	NPC61442
0.7476	Intermediate Similarity	NPC473523
0.7475	Intermediate Similarity	NPC471362
0.7475	Intermediate Similarity	NPC241047
0.7475	Intermediate Similarity	NPC259042
0.7475	Intermediate Similarity	NPC157686
0.7475	Intermediate Similarity	NPC471372
0.7475	Intermediate Similarity	NPC472189
0.7475	Intermediate Similarity	NPC276110
0.7474	Intermediate Similarity	NPC471779
0.7474	Intermediate Similarity	NPC166857
0.7453	Intermediate Similarity	NPC40728
0.7453	Intermediate Similarity	NPC316974
0.7451	Intermediate Similarity	NPC475617
0.7451	Intermediate Similarity	NPC49532
0.7451	Intermediate Similarity	NPC308824
0.7449	Intermediate Similarity	NPC474835
0.7449	Intermediate Similarity	NPC470187
0.7449	Intermediate Similarity	NPC26046
0.7449	Intermediate Similarity	NPC7349
0.7447	Intermediate Similarity	NPC164424
0.7429	Intermediate Similarity	NPC475781
0.7429	Intermediate Similarity	NPC88013
0.7429	Intermediate Similarity	NPC122816
0.7429	Intermediate Similarity	NPC125423
0.7429	Intermediate Similarity	NPC475074
0.7423	Intermediate Similarity	NPC474323
0.7423	Intermediate Similarity	NPC48732
0.7423	Intermediate Similarity	NPC194485
0.7423	Intermediate Similarity	NPC209816
0.7423	Intermediate Similarity	NPC153853
0.7423	Intermediate Similarity	NPC53890
0.7423	Intermediate Similarity	NPC206614
0.7423	Intermediate Similarity	NPC219937
0.7423	Intermediate Similarity	NPC123252
0.7416	Intermediate Similarity	NPC136424
0.7416	Intermediate Similarity	NPC329626
0.7416	Intermediate Similarity	NPC293223
0.7407	Intermediate Similarity	NPC321272
0.7407	Intermediate Similarity	NPC317460
0.7407	Intermediate Similarity	NPC470025
0.7407	Intermediate Similarity	NPC328074
0.7404	Intermediate Similarity	NPC470062
0.7404	Intermediate Similarity	NPC470064
0.7404	Intermediate Similarity	NPC470321
0.7404	Intermediate Similarity	NPC470060
0.7404	Intermediate Similarity	NPC31430
0.7404	Intermediate Similarity	NPC470058
0.7404	Intermediate Similarity	NPC473207
0.7404	Intermediate Similarity	NPC81567
0.7404	Intermediate Similarity	NPC85593
0.7404	Intermediate Similarity	NPC201880
0.7404	Intermediate Similarity	NPC470043
0.7404	Intermediate Similarity	NPC264867
0.7404	Intermediate Similarity	NPC470057
0.7404	Intermediate Similarity	NPC470059
0.7404	Intermediate Similarity	NPC470061
0.74	Intermediate Similarity	NPC165632
0.74	Intermediate Similarity	NPC111834
0.74	Intermediate Similarity	NPC306797
0.74	Intermediate Similarity	NPC171598
0.74	Intermediate Similarity	NPC472995
0.74	Intermediate Similarity	NPC169270
0.74	Intermediate Similarity	NPC475304
0.74	Intermediate Similarity	NPC93245
0.74	Intermediate Similarity	NPC292718
0.7396	Intermediate Similarity	NPC242448
0.7396	Intermediate Similarity	NPC160304
0.7396	Intermediate Similarity	NPC309656
0.7396	Intermediate Similarity	NPC263079
0.7383	Intermediate Similarity	NPC177047
0.7379	Intermediate Similarity	NPC475344
0.7379	Intermediate Similarity	NPC11956
0.7379	Intermediate Similarity	NPC470972
0.7379	Intermediate Similarity	NPC476471
0.7374	Intermediate Similarity	NPC39453
0.7374	Intermediate Similarity	NPC24861
0.7374	Intermediate Similarity	NPC469596
0.7374	Intermediate Similarity	NPC105490
0.7374	Intermediate Similarity	NPC225474
0.7374	Intermediate Similarity	NPC148000
0.7368	Intermediate Similarity	NPC162071
0.7368	Intermediate Similarity	NPC102996
0.7358	Intermediate Similarity	NPC311223
0.7358	Intermediate Similarity	NPC470024
0.7358	Intermediate Similarity	NPC255082
0.7358	Intermediate Similarity	NPC181994
0.7353	Intermediate Similarity	NPC16601
0.7353	Intermediate Similarity	NPC271295
0.7353	Intermediate Similarity	NPC79303
0.7347	Intermediate Similarity	NPC208839
0.7347	Intermediate Similarity	NPC219516
0.7347	Intermediate Similarity	NPC249034
0.7347	Intermediate Similarity	NPC41838
0.7347	Intermediate Similarity	NPC165180
0.734	Intermediate Similarity	NPC299963
0.7339	Intermediate Similarity	NPC470027
0.7339	Intermediate Similarity	NPC474410
0.7339	Intermediate Similarity	NPC293658

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 NPC8729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	2326
0.2-0.3	3890
0.3-0.4	1951
0.4-0.5	485
0.5-0.6	256
0.6-0.7	47
0.7-0.8	0
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
0.7282	Intermediate Similarity	NPD5344	Discontinued
0.7184	Intermediate Similarity	NPD6648	Approved
0.693	Remote Similarity	NPD7328	Approved
0.693	Remote Similarity	NPD7327	Approved
0.6923	Remote Similarity	NPD4225	Approved
0.6897	Remote Similarity	NPD8033	Approved
0.6875	Remote Similarity	NPD8133	Approved
0.687	Remote Similarity	NPD7516	Approved
0.6857	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD7639	Approved
0.681	Remote Similarity	NPD8294	Approved
0.681	Remote Similarity	NPD8377	Approved
0.6762	Remote Similarity	NPD7638	Approved
0.6752	Remote Similarity	NPD8378	Approved
0.6752	Remote Similarity	NPD8296	Approved
0.6752	Remote Similarity	NPD8380	Approved
0.6752	Remote Similarity	NPD8335	Approved
0.6752	Remote Similarity	NPD8379	Approved
0.6577	Remote Similarity	NPD6686	Approved
0.6577	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3168	Discontinued
0.6529	Remote Similarity	NPD7507	Approved
0.6518	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8513	Phase 3
0.6471	Remote Similarity	NPD7503	Approved
0.6471	Remote Similarity	NPD8516	Approved
0.6471	Remote Similarity	NPD8517	Approved
0.6471	Remote Similarity	NPD8515	Approved
0.646	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7632	Discontinued
0.6408	Remote Similarity	NPD46	Approved
0.6408	Remote Similarity	NPD7838	Discovery
0.6408	Remote Similarity	NPD6698	Approved
0.6404	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1145	Discontinued
0.6371	Remote Similarity	NPD7319	Approved
0.6346	Remote Similarity	NPD8035	Phase 2
0.6346	Remote Similarity	NPD8034	Phase 2
0.6339	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7492	Approved
0.6304	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4250	Approved
0.6275	Remote Similarity	NPD4251	Approved
0.6275	Remote Similarity	NPD7524	Approved
0.6271	Remote Similarity	NPD7115	Discovery
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6059	Approved
0.6228	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8074	Phase 3
0.621	Remote Similarity	NPD7078	Approved
0.621	Remote Similarity	NPD8293	Discontinued
0.6207	Remote Similarity	NPD6053	Discontinued
0.62	Remote Similarity	NPD6695	Phase 3
0.62	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3669	Approved
0.6195	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4249	Approved
0.616	Remote Similarity	NPD7736	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.6139	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5779	Approved
0.6132	Remote Similarity	NPD5778	Approved
0.6132	Remote Similarity	NPD6399	Phase 3
0.6106	Remote Similarity	NPD6008	Approved
0.6106	Remote Similarity	NPD5357	Phase 1
0.6078	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6016	Approved
0.6066	Remote Similarity	NPD6015	Approved
0.6061	Remote Similarity	NPD7525	Registered
0.6053	Remote Similarity	NPD6412	Phase 2
0.6038	Remote Similarity	NPD7983	Approved
0.6038	Remote Similarity	NPD7637	Suspended
0.6034	Remote Similarity	NPD6371	Approved
0.6016	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD1695	Approved
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5739	Approved
0.5965	Remote Similarity	NPD7128	Approved
0.5965	Remote Similarity	NPD6402	Approved
0.5965	Remote Similarity	NPD6675	Approved
0.5962	Remote Similarity	NPD7750	Discontinued
0.5938	Remote Similarity	NPD1811	Approved
0.5938	Remote Similarity	NPD1810	Approved
0.5935	Remote Similarity	NPD6921	Approved
0.5932	Remote Similarity	NPD8297	Approved
0.5932	Remote Similarity	NPD6882	Approved
0.5926	Remote Similarity	NPD7748	Approved
0.5922	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7902	Approved
0.59	Remote Similarity	NPD4820	Approved
0.59	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6928	Phase 2
0.59	Remote Similarity	NPD6930	Phase 2
0.59	Remote Similarity	NPD4819	Approved
0.59	Remote Similarity	NPD4821	Approved
0.59	Remote Similarity	NPD6931	Approved
0.59	Remote Similarity	NPD4822	Approved
0.5893	Remote Similarity	NPD1700	Approved
0.5882	Remote Similarity	NPD4632	Approved
0.5862	Remote Similarity	NPD6899	Approved
0.5862	Remote Similarity	NPD6881	Approved
0.5854	Remote Similarity	NPD6319	Approved
0.584	Remote Similarity	NPD6067	Discontinued
0.584	Remote Similarity	NPD8328	Phase 3
0.5833	Remote Similarity	NPD8171	Discontinued
0.5824	Remote Similarity	NPD371	Approved
0.5818	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6373	Approved
0.5812	Remote Similarity	NPD6372	Approved
0.58	Remote Similarity	NPD6929	Approved
0.58	Remote Similarity	NPD7645	Phase 2
0.5789	Remote Similarity	NPD2687	Approved
0.5789	Remote Similarity	NPD2254	Approved
0.5789	Remote Similarity	NPD2686	Approved
0.5781	Remote Similarity	NPD6033	Approved
0.578	Remote Similarity	NPD5282	Discontinued
0.5776	Remote Similarity	NPD5701	Approved
0.5776	Remote Similarity	NPD5697	Approved
0.5763	Remote Similarity	NPD7102	Approved
0.5763	Remote Similarity	NPD6883	Approved
0.5763	Remote Similarity	NPD7290	Approved
0.5741	Remote Similarity	NPD7515	Phase 2
0.5741	Remote Similarity	NPD7087	Discontinued
0.5728	Remote Similarity	NPD5362	Discontinued
0.5728	Remote Similarity	NPD7154	Phase 3
0.5727	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD6617	Approved
0.5714	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD6650	Approved
0.5701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6101	Approved
0.57	Remote Similarity	NPD4271	Approved
0.57	Remote Similarity	NPD6697	Approved
0.57	Remote Similarity	NPD4268	Approved
0.57	Remote Similarity	NPD6114	Approved
0.57	Remote Similarity	NPD6118	Approved
0.57	Remote Similarity	NPD6115	Approved
0.5686	Remote Similarity	NPD1779	Approved
0.5686	Remote Similarity	NPD1780	Approved
0.568	Remote Similarity	NPD5983	Phase 2
0.568	Remote Similarity	NPD8269	Approved
0.568	Remote Similarity	NPD8267	Approved
0.568	Remote Similarity	NPD8266	Approved
0.568	Remote Similarity	NPD8268	Approved
0.5678	Remote Similarity	NPD6012	Approved
0.5678	Remote Similarity	NPD6013	Approved
0.5678	Remote Similarity	NPD6014	Approved
0.5676	Remote Similarity	NPD7839	Suspended
0.566	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7900	Approved
0.5631	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6083	Phase 2
0.5625	Remote Similarity	NPD6336	Discontinued
0.5625	Remote Similarity	NPD6084	Phase 2
0.5619	Remote Similarity	NPD6893	Approved
0.5619	Remote Similarity	NPD1694	Approved
0.5614	Remote Similarity	NPD4159	Approved
0.5603	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5776	Phase 2
0.56	Remote Similarity	NPD6116	Phase 1
0.56	Remote Similarity	NPD6925	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