NPASS Compound

Structure

CID256368 OpenBabel06191716062D 39 42 0 0 1 0 0 0 0 0999 V2000 4.4586 -3.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4315 -2.5387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2317 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1285 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6456 -1.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0356 -1.1804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1247 -1.5941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7585 -1.6665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2620 -1.7924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1398 -0.6306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7266 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3246 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3246 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0720 -1.3690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5926 -1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2765 -2.1344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2296 -0.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4586 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7381 -1.8181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2420 -0.8359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3385 -2.0363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5926 -0.6045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2627 -2.2837 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0363 0.2486 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0599 -0.0768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6830 0.6825 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9051 0.7438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0126 0.2270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3439 1.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -1.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4586 -0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8213 -2.2497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8045 0.4211 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 20 1 0 0 0 0 3 22 2 0 0 0 0 4 35 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 10 2 0 0 0 0 8 23 1 0 0 0 0 10 29 1 0 0 0 0 11 13 2 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 14 36 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 26 1 0 0 0 0 19 28 1 0 0 0 0 21 2 1 1 0 0 0 23 7 1 6 0 0 0 23 37 1 0 0 0 0 24 11 1 1 0 0 0 24 36 1 0 0 0 0 25 9 1 1 0 0 0 25 37 1 0 0 0 0 26 30 1 0 0 0 0 26 32 1 6 0 0 0 27 19 1 1 0 0 0 27 30 1 0 0 0 0 27 39 1 0 0 0 0 28 31 1 1 0 0 0 28 38 1 0 0 0 0 29 33 2 0 0 0 0 29 38 1 0 0 0 0 30 34 1 6 0 0 0 31 13 1 1 0 0 0 31 35 1 0 0 0 0 31 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.3
Volume:	565.009
LogP:	4.481
LogD:	3.18
LogS:	-4.565
# Rotatable Bonds:	3
TPSA:	103.68
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	7.36
Fsp3:	0.645
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.808
MDCK Permeability:	5.1064256695099175e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.064
Human Intestinal Absorption (HIA):	0.412
20% Bioavailability (F20%):	0.706
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	63.46997833251953%
Volume Distribution (VD):	1.092
Pgp-substrate:	14.868217468261719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.23
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.658
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	6.145
Half-life (T1/2):	0.406

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.941
Drug-inuced Liver Injury (DILI):	0.403
AMES Toxicity:	0.967
Rat Oral Acute Toxicity:	0.312
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.927
Carcinogencity:	0.959
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.74

Download Data

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

Natural Product: NPC256368

Natural Product ID:	NPC256368
*Common Name:**	SZVPVYZZKFBESC-ROKXZQSJSA-N
IUPAC Name:	n.a.
Synonyms:	20-Methoxy-Fijianolide A
Standard InCHIKey:	SZVPVYZZKFBESC-ROKXZQSJSA-N
Standard InCHI:	InChI=1S/C31H44O8/c1-20-12-14-36-24(16-20)11-13-31(35-4)28-19-27(39-31)30(34)26(32)18-22(3)15-21(2)17-25-9-5-7-23(37-25)8-6-10-29(33)38-28/h5-7,10-13,21,23-28,30,32,34H,3,8-9,14-19H2,1-2,4H3/b10-6-,13-11+/t21-,23-,24+,25-,26-,27+,28-,30-,31+/m0/s1
SMILES:	CO[C@]1(/C=C/[C@H]2OCC=C(C2)C)O[C@@H]2C[C@@H]1OC(=O)/C=CC[C@@H]1C=CC[C@H](O1)C[C@H](CC(=C)C[C@@H]([C@@H]2O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934279
PubChem CID:	56649407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	Tongan	n.a.	PMID[19877653]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22129061]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30371079]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[534776]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[534776]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[534776]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	2.5	ug.mL-1	PMID[534776]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	>	10.0	ug.mL-1	PMID[534776]

☑ 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 NPC256368 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	190
0.1-0.2	1141
0.2-0.3	4337
0.3-0.4	9985
0.4-0.5	13641
0.5-0.6	7984
0.6-0.7	4278
0.7-0.8	1121
0.8-0.85	16
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC177668
0.954	High Similarity	NPC133450
0.9	High Similarity	NPC3952
0.8632	High Similarity	NPC475332
0.8602	High Similarity	NPC238090
0.8602	High Similarity	NPC472196
0.8602	High Similarity	NPC472195
0.8556	High Similarity	NPC311163
0.8511	High Similarity	NPC159698
0.8444	Intermediate Similarity	NPC471494
0.8391	Intermediate Similarity	NPC139712
0.8351	Intermediate Similarity	NPC203627
0.8333	Intermediate Similarity	NPC173329
0.8333	Intermediate Similarity	NPC288350
0.8333	Intermediate Similarity	NPC266718
0.8283	Intermediate Similarity	NPC201191
0.8261	Intermediate Similarity	NPC313658
0.8261	Intermediate Similarity	NPC316138
0.8218	Intermediate Similarity	NPC239961
0.82	Intermediate Similarity	NPC197736
0.8191	Intermediate Similarity	NPC471569
0.8191	Intermediate Similarity	NPC202886
0.8182	Intermediate Similarity	NPC471637
0.8182	Intermediate Similarity	NPC180725
0.8182	Intermediate Similarity	NPC57586
0.8182	Intermediate Similarity	NPC475157
0.8182	Intermediate Similarity	NPC154132
0.8182	Intermediate Similarity	NPC2313
0.8182	Intermediate Similarity	NPC475655
0.8182	Intermediate Similarity	NPC198992
0.8161	Intermediate Similarity	NPC474026
0.8105	Intermediate Similarity	NPC206679
0.8105	Intermediate Similarity	NPC477749
0.8105	Intermediate Similarity	NPC114172
0.8105	Intermediate Similarity	NPC471324
0.8095	Intermediate Similarity	NPC470025
0.8095	Intermediate Similarity	NPC328074
0.8095	Intermediate Similarity	NPC321272
0.8095	Intermediate Similarity	NPC317460
0.809	Intermediate Similarity	NPC133226
0.809	Intermediate Similarity	NPC470147
0.8085	Intermediate Similarity	NPC477748
0.8077	Intermediate Similarity	NPC316708
0.8068	Intermediate Similarity	NPC248775
0.8061	Intermediate Similarity	NPC120299
0.8041	Intermediate Similarity	NPC471141
0.8041	Intermediate Similarity	NPC36954
0.8039	Intermediate Similarity	NPC315070
0.8022	Intermediate Similarity	NPC44261
0.8022	Intermediate Similarity	NPC27314
0.8022	Intermediate Similarity	NPC263087
0.8022	Intermediate Similarity	NPC2379
0.8022	Intermediate Similarity	NPC106912
0.8022	Intermediate Similarity	NPC31019
0.8021	Intermediate Similarity	NPC189651
0.8021	Intermediate Similarity	NPC475098
0.8021	Intermediate Similarity	NPC471483
0.8021	Intermediate Similarity	NPC476300
0.8021	Intermediate Similarity	NPC109406
0.8021	Intermediate Similarity	NPC159092
0.8019	Intermediate Similarity	NPC470027
0.8	Intermediate Similarity	NPC17791
0.8	Intermediate Similarity	NPC8538
0.8	Intermediate Similarity	NPC184208
0.8	Intermediate Similarity	NPC469469
0.8	Intermediate Similarity	NPC470026
0.7981	Intermediate Similarity	NPC133625
0.798	Intermediate Similarity	NPC65700
0.798	Intermediate Similarity	NPC187268
0.798	Intermediate Similarity	NPC475653
0.7978	Intermediate Similarity	NPC470149
0.7978	Intermediate Similarity	NPC470148
0.7961	Intermediate Similarity	NPC109376
0.7959	Intermediate Similarity	NPC306041
0.7959	Intermediate Similarity	NPC472995
0.7959	Intermediate Similarity	NPC255410
0.7957	Intermediate Similarity	NPC208473
0.7957	Intermediate Similarity	NPC186332
0.7957	Intermediate Similarity	NPC47220
0.7955	Intermediate Similarity	NPC475711
0.7941	Intermediate Similarity	NPC472748
0.7917	Intermediate Similarity	NPC476084
0.7917	Intermediate Similarity	NPC184463
0.7917	Intermediate Similarity	NPC476075
0.7917	Intermediate Similarity	NPC30515
0.7885	Intermediate Similarity	NPC128795
0.7885	Intermediate Similarity	NPC392
0.7885	Intermediate Similarity	NPC470024
0.7885	Intermediate Similarity	NPC219900
0.7885	Intermediate Similarity	NPC135015
0.7885	Intermediate Similarity	NPC177524
0.7885	Intermediate Similarity	NPC48548
0.7885	Intermediate Similarity	NPC224660
0.7885	Intermediate Similarity	NPC217921
0.7879	Intermediate Similarity	NPC472998
0.7879	Intermediate Similarity	NPC266842
0.7879	Intermediate Similarity	NPC471490
0.7872	Intermediate Similarity	NPC199382
0.7872	Intermediate Similarity	NPC471055
0.7872	Intermediate Similarity	NPC471056
0.7864	Intermediate Similarity	NPC218158
0.7864	Intermediate Similarity	NPC172867
0.7864	Intermediate Similarity	NPC472751
0.7864	Intermediate Similarity	NPC82251
0.7864	Intermediate Similarity	NPC472749
0.7857	Intermediate Similarity	NPC300710
0.785	Intermediate Similarity	NPC264153
0.785	Intermediate Similarity	NPC287075
0.7849	Intermediate Similarity	NPC470124
0.7843	Intermediate Similarity	NPC472747
0.7843	Intermediate Similarity	NPC281378
0.7843	Intermediate Similarity	NPC472750
0.7841	Intermediate Similarity	NPC469880
0.7835	Intermediate Similarity	NPC475912
0.7835	Intermediate Similarity	NPC156553
0.7835	Intermediate Similarity	NPC61201
0.783	Intermediate Similarity	NPC297945
0.783	Intermediate Similarity	NPC126897
0.7822	Intermediate Similarity	NPC219038
0.7812	Intermediate Similarity	NPC474761
0.7812	Intermediate Similarity	NPC51004
0.7812	Intermediate Similarity	NPC118078
0.7812	Intermediate Similarity	NPC476004
0.7812	Intermediate Similarity	NPC327253
0.7812	Intermediate Similarity	NPC473448
0.781	Intermediate Similarity	NPC313668
0.781	Intermediate Similarity	NPC206618
0.781	Intermediate Similarity	NPC316974
0.781	Intermediate Similarity	NPC40728
0.781	Intermediate Similarity	NPC315836
0.7802	Intermediate Similarity	NPC473339
0.7802	Intermediate Similarity	NPC315731
0.7802	Intermediate Similarity	NPC471552
0.7788	Intermediate Similarity	NPC88013
0.7788	Intermediate Similarity	NPC125423
0.7778	Intermediate Similarity	NPC54731
0.7778	Intermediate Similarity	NPC279621
0.7778	Intermediate Similarity	NPC476315
0.7755	Intermediate Similarity	NPC472198
0.7755	Intermediate Similarity	NPC469491
0.7755	Intermediate Similarity	NPC71589
0.7745	Intermediate Similarity	NPC471599
0.7745	Intermediate Similarity	NPC195510
0.7745	Intermediate Similarity	NPC473596
0.7745	Intermediate Similarity	NPC13171
0.7745	Intermediate Similarity	NPC121423
0.7742	Intermediate Similarity	NPC160517
0.7742	Intermediate Similarity	NPC473308
0.7742	Intermediate Similarity	NPC475035
0.7742	Intermediate Similarity	NPC78673
0.7742	Intermediate Similarity	NPC186155
0.7736	Intermediate Similarity	NPC177047
0.7732	Intermediate Similarity	NPC472199
0.7732	Intermediate Similarity	NPC158061
0.7732	Intermediate Similarity	NPC472010
0.7732	Intermediate Similarity	NPC472197
0.7727	Intermediate Similarity	NPC285840
0.7727	Intermediate Similarity	NPC327041
0.7723	Intermediate Similarity	NPC244878
0.7723	Intermediate Similarity	NPC130792
0.7717	Intermediate Similarity	NPC251026
0.7714	Intermediate Similarity	NPC38948
0.7714	Intermediate Similarity	NPC311223
0.7708	Intermediate Similarity	NPC307411
0.7701	Intermediate Similarity	NPC327383
0.7701	Intermediate Similarity	NPC185186
0.77	Intermediate Similarity	NPC98112
0.77	Intermediate Similarity	NPC239547
0.77	Intermediate Similarity	NPC91197
0.77	Intermediate Similarity	NPC309503
0.77	Intermediate Similarity	NPC155319
0.77	Intermediate Similarity	NPC2666
0.77	Intermediate Similarity	NPC40812
0.77	Intermediate Similarity	NPC125551
0.77	Intermediate Similarity	NPC96597
0.7692	Intermediate Similarity	NPC93026
0.7692	Intermediate Similarity	NPC265502
0.7692	Intermediate Similarity	NPC29389
0.7692	Intermediate Similarity	NPC476740
0.7692	Intermediate Similarity	NPC469960
0.7692	Intermediate Similarity	NPC476738
0.7684	Intermediate Similarity	NPC475037
0.7677	Intermediate Similarity	NPC471492
0.7677	Intermediate Similarity	NPC14961
0.7677	Intermediate Similarity	NPC286612
0.7677	Intermediate Similarity	NPC230347
0.7677	Intermediate Similarity	NPC270013
0.7677	Intermediate Similarity	NPC275310
0.7677	Intermediate Similarity	NPC170204
0.7677	Intermediate Similarity	NPC469583
0.767	Intermediate Similarity	NPC7613
0.767	Intermediate Similarity	NPC7644
0.767	Intermediate Similarity	NPC309398
0.767	Intermediate Similarity	NPC127933
0.767	Intermediate Similarity	NPC475889
0.7667	Intermediate Similarity	NPC326753
0.766	Intermediate Similarity	NPC242233
0.7653	Intermediate Similarity	NPC212486
0.7653	Intermediate Similarity	NPC81419
0.7653	Intermediate Similarity	NPC320552

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 NPC256368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1495
0.2-0.3	3835
0.3-0.4	2508
0.4-0.5	785
0.5-0.6	286
0.6-0.7	76
0.7-0.8	8
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
0.8387	Intermediate Similarity	NPD7838	Discovery
0.8163	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6698	Approved
0.8	Intermediate Similarity	NPD46	Approved
0.7885	Intermediate Similarity	NPD6686	Approved
0.783	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5344	Discontinued
0.7368	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7503	Approved
0.729	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4225	Approved
0.7212	Intermediate Similarity	NPD6648	Approved
0.72	Intermediate Similarity	NPD7983	Approved
0.7105	Intermediate Similarity	NPD7328	Approved
0.7105	Intermediate Similarity	NPD7327	Approved
0.7069	Intermediate Similarity	NPD8513	Phase 3
0.7069	Intermediate Similarity	NPD8033	Approved
0.7043	Intermediate Similarity	NPD7516	Approved
0.6983	Remote Similarity	NPD8377	Approved
0.6983	Remote Similarity	NPD8294	Approved
0.6937	Remote Similarity	NPD6371	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD8296	Approved
0.6923	Remote Similarity	NPD8378	Approved
0.6923	Remote Similarity	NPD8335	Approved
0.6923	Remote Similarity	NPD8515	Approved
0.6923	Remote Similarity	NPD8380	Approved
0.6923	Remote Similarity	NPD8379	Approved
0.6814	Remote Similarity	NPD6053	Discontinued
0.6807	Remote Similarity	NPD7830	Approved
0.6807	Remote Similarity	NPD7829	Approved
0.68	Remote Similarity	NPD4251	Approved
0.68	Remote Similarity	NPD4250	Approved
0.6792	Remote Similarity	NPD7638	Approved
0.6729	Remote Similarity	NPD7639	Approved
0.6729	Remote Similarity	NPD7640	Approved
0.67	Remote Similarity	NPD4249	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8074	Phase 3
0.6635	Remote Similarity	NPD5778	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.6604	Remote Similarity	NPD7839	Suspended
0.66	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7115	Discovery
0.6566	Remote Similarity	NPD7154	Phase 3
0.6562	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7637	Suspended
0.6532	Remote Similarity	NPD7319	Approved
0.6529	Remote Similarity	NPD7642	Approved
0.6525	Remote Similarity	NPD7641	Discontinued
0.6471	Remote Similarity	NPD7524	Approved
0.6442	Remote Similarity	NPD5785	Approved
0.6441	Remote Similarity	NPD7505	Discontinued
0.6436	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD4819	Approved
0.6423	Remote Similarity	NPD8451	Approved
0.6404	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4268	Approved
0.6392	Remote Similarity	NPD4271	Approved
0.6371	Remote Similarity	NPD8448	Approved
0.6364	Remote Similarity	NPD8444	Approved
0.6346	Remote Similarity	NPD1695	Approved
0.6341	Remote Similarity	NPD7492	Approved
0.6337	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD8133	Approved
0.63	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6616	Approved
0.6281	Remote Similarity	NPD6054	Approved
0.6275	Remote Similarity	NPD5363	Approved
0.6275	Remote Similarity	NPD1694	Approved
0.6262	Remote Similarity	NPD5282	Discontinued
0.624	Remote Similarity	NPD7078	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6238	Remote Similarity	NPD5362	Discontinued
0.6238	Remote Similarity	NPD6695	Phase 3
0.622	Remote Similarity	NPD8390	Approved
0.622	Remote Similarity	NPD8391	Approved
0.622	Remote Similarity	NPD8392	Approved
0.621	Remote Similarity	NPD8341	Approved
0.621	Remote Similarity	NPD8299	Approved
0.621	Remote Similarity	NPD8342	Approved
0.621	Remote Similarity	NPD8340	Approved
0.6207	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7736	Approved
0.619	Remote Similarity	NPD6101	Approved
0.6179	Remote Similarity	NPD6370	Approved
0.617	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7500	Approved
0.6167	Remote Similarity	NPD6009	Approved
0.6161	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6319	Approved
0.614	Remote Similarity	NPD4211	Phase 1
0.6139	Remote Similarity	NPD6435	Approved
0.6129	Remote Similarity	NPD8328	Phase 3
0.6121	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8297	Approved
0.6098	Remote Similarity	NPD6016	Approved
0.6098	Remote Similarity	NPD6015	Approved
0.6078	Remote Similarity	NPD5331	Approved
0.6078	Remote Similarity	NPD6110	Phase 1
0.6078	Remote Similarity	NPD5332	Approved
0.6075	Remote Similarity	NPD6411	Approved
0.605	Remote Similarity	NPD4632	Approved
0.6048	Remote Similarity	NPD8080	Discontinued
0.6048	Remote Similarity	NPD5125	Phase 3
0.6048	Remote Similarity	NPD5988	Approved
0.6048	Remote Similarity	NPD5126	Approved
0.6047	Remote Similarity	NPD7260	Phase 2
0.604	Remote Similarity	NPD4790	Discontinued
0.6033	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD8273	Phase 1
0.6016	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD6929	Approved
0.5984	Remote Similarity	NPD8293	Discontinued
0.5981	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD3168	Discontinued
0.598	Remote Similarity	NPD4270	Approved
0.598	Remote Similarity	NPD5209	Approved
0.598	Remote Similarity	NPD4269	Approved
0.5948	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6931	Approved
0.5941	Remote Similarity	NPD7514	Phase 3
0.5941	Remote Similarity	NPD5368	Approved
0.5941	Remote Similarity	NPD7332	Phase 2
0.5941	Remote Similarity	NPD6930	Phase 2
0.5932	Remote Similarity	NPD6421	Discontinued
0.5912	Remote Similarity	NPD7266	Discontinued
0.5905	Remote Similarity	NPD5786	Approved
0.5902	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.59	Remote Similarity	NPD7145	Approved
0.59	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6881	Approved
0.5897	Remote Similarity	NPD6899	Approved
0.5897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6051	Approved
0.5882	Remote Similarity	NPD6902	Approved
0.5882	Remote Similarity	NPD6649	Approved
0.5882	Remote Similarity	NPD5369	Approved
0.5882	Remote Similarity	NPD6650	Approved
0.5872	Remote Similarity	NPD6399	Phase 3
0.5862	Remote Similarity	NPD6640	Phase 3
0.5859	Remote Similarity	NPD6933	Approved
0.584	Remote Similarity	NPD8266	Approved
0.584	Remote Similarity	NPD8269	Approved
0.584	Remote Similarity	NPD8268	Approved
0.584	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8267	Approved
0.5833	Remote Similarity	NPD969	Suspended
0.5812	Remote Similarity	NPD5697	Approved
0.5804	Remote Similarity	NPD6084	Phase 2
0.5804	Remote Similarity	NPD6083	Phase 2
0.58	Remote Similarity	NPD5776	Phase 2
0.58	Remote Similarity	NPD6925	Approved
0.58	Remote Similarity	NPD6932	Approved
0.5798	Remote Similarity	NPD7290	Approved
0.5798	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD7102	Approved
0.5789	Remote Similarity	NPD8415	Approved
0.5784	Remote Similarity	NPD4252	Approved
0.578	Remote Similarity	NPD7087	Discontinued
0.576	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8039	Approved
0.5758	Remote Similarity	NPD6845	Suspended
0.575	Remote Similarity	NPD6617	Approved
0.575	Remote Similarity	NPD6869	Approved
0.575	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD8130	Phase 1
0.5748	Remote Similarity	NPD6067	Discontinued
0.5748	Remote Similarity	NPD7604	Phase 2
0.5746	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6675	Approved
0.5726	Remote Similarity	NPD5739	Approved
0.5726	Remote Similarity	NPD7128	Approved
0.5726	Remote Similarity	NPD6402	Approved
0.5725	Remote Similarity	NPD5956	Approved
0.5714	Remote Similarity	NPD1145	Discontinued
0.5714	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5699	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.569	Remote Similarity	NPD1407	Approved
0.569	Remote Similarity	NPD6647	Phase 2
0.5678	Remote Similarity	NPD6685	Approved
0.5676	Remote Similarity	NPD7748	Approved
0.5674	Remote Similarity	NPD7625	Phase 1

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