NPASS Compound

Structure

NPC88507 OpenBabel07101718222D 35 37 0 0 1 0 0 0 0 0999 V2000 2.2022 3.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7520 1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7783 2.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7005 -0.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6991 -0.5577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0181 -2.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3441 1.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3589 4.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7783 1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5157 3.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3178 1.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0140 -0.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8309 1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1708 0.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3276 2.5147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0140 2.5147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2915 1.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8573 0.0805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0000 0.3684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9705 -2.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1708 3.0016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3276 1.5410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0140 1.5410 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3276 4.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3960 0.8895 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9684 0.1018 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8573 1.0542 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1708 1.0542 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9524 0.5708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6220 -2.9950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3276 5.4358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3484 1.0919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2714 -1.3454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1708 3.9752 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 8 1 0 0 0 0 2 9 2 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 8 10 1 0 0 0 0 9 17 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 27 1 0 0 0 0 15 21 1 0 0 0 0 15 22 2 0 0 0 0 16 21 1 0 0 0 0 16 23 1 0 0 0 0 18 27 1 1 0 0 0 19 29 2 0 0 0 0 19 32 1 0 0 0 0 20 30 2 0 0 0 0 20 33 1 0 0 0 0 21 34 1 1 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 27 1 6 0 0 0 23 28 1 0 0 0 0 24 31 2 0 0 0 0 24 34 1 0 0 0 0 25 32 1 1 0 0 0 25 35 1 0 0 0 0 26 28 1 1 0 0 0 26 33 1 0 0 0 0 26 35 1 0 0 0 0 27 7 1 6 0 0 0 28 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.28
Volume:	512.888
LogP:	4.704
LogD:	3.867
LogS:	-5.236
# Rotatable Bonds:	11
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	5.575
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.61
MDCK Permeability:	7.698142144363374e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.121
30% Bioavailability (F30%):	0.491

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	92.00516510009766%
Volume Distribution (VD):	2.19
Pgp-substrate:	5.182101726531982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.361
CYP2C19-substrate:	0.235
CYP2C9-inhibitor:	0.344
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	3.631
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.94
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.987
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.653
Carcinogencity:	0.616
Eye Corrosion:	0.273
Eye Irritation:	0.187
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC88507

Natural Product ID:	NPC88507
*Common Name:**	Caseargrewins E
IUPAC Name:	[(1S,3R,5R,6aS,7R,8R,10aS)-1,3-diacetyloxy-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] butanoate
Synonyms:	caseargrewins E
Standard InCHIKey:	UIVLKULAENGHMF-QSBPWGSHSA-N
Standard InCHI:	InChI=1S/C28H40O7/c1-8-10-24(31)34-21-15-22-25(32-19(5)29)35-26(33-20(6)30)28(22)14-12-18(4)27(7,23(28)16-21)13-11-17(3)9-2/h9,11,15,18,21,23,25-26H,2,8,10,12-14,16H2,1,3-7H3/b17-11-/t18-,21+,23+,25+,26-,27-,28-/m1/s1
SMILES:	CCCC(=O)O[C@H]1C=C2[C@@H](OC(=O)C)O[C@H]([C@@]32CC[C@@H](C)[C@@](C)(C/C=C(/C)C=C)[C@@H]3C1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL396763
PubChem CID:	16756783
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	bark	in the campus of Khon Kaen University, Khon Kaen, Thailand	2001-SEP	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	bark	n.a.	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17567069]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26516994]

☑ 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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.66	ug.mL-1	PMID[512618]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	0.15	ug.mL-1	PMID[512618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.91	ug.mL-1	PMID[512618]

☑ 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 NPC88507 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	206
0.1-0.2	1017
0.2-0.3	4214
0.3-0.4	10911
0.4-0.5	11881
0.5-0.6	7763
0.6-0.7	5836
0.7-0.8	741
0.8-0.85	47
0.85-0.9	41
0.9-0.95	38
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC311166
0.9457	High Similarity	NPC473204
0.9451	High Similarity	NPC472188
0.9348	High Similarity	NPC318917
0.9348	High Similarity	NPC471366
0.9348	High Similarity	NPC472186
0.9348	High Similarity	NPC476800
0.9247	High Similarity	NPC472187
0.9247	High Similarity	NPC473545
0.9239	High Similarity	NPC98112
0.9231	High Similarity	NPC471362
0.9231	High Similarity	NPC472189
0.9231	High Similarity	NPC471372
0.9158	High Similarity	NPC134270
0.913	High Similarity	NPC171598
0.9062	High Similarity	NPC473207
0.9062	High Similarity	NPC81567
0.9062	High Similarity	NPC201880
0.9062	High Similarity	NPC264867
0.9062	High Similarity	NPC470321
0.9053	High Similarity	NPC238397
0.9053	High Similarity	NPC471363
0.8969	High Similarity	NPC252296
0.8958	High Similarity	NPC7613
0.8958	High Similarity	NPC127933
0.8958	High Similarity	NPC7644
0.8958	High Similarity	NPC475889
0.8878	High Similarity	NPC184512
0.8788	High Similarity	NPC311223
0.8723	High Similarity	NPC94905
0.8723	High Similarity	NPC8954
0.87	High Similarity	NPC316974
0.8687	High Similarity	NPC88013
0.8687	High Similarity	NPC125423
0.8681	High Similarity	NPC293044
0.8614	High Similarity	NPC119550
0.86	High Similarity	NPC48548
0.86	High Similarity	NPC128795
0.86	High Similarity	NPC135015
0.86	High Similarity	NPC217921
0.8586	High Similarity	NPC172867
0.8526	High Similarity	NPC112654
0.8515	High Similarity	NPC40728
0.8506	High Similarity	NPC473685
0.85	High Similarity	NPC109376
0.8416	Intermediate Similarity	NPC470024
0.8416	Intermediate Similarity	NPC224660
0.84	Intermediate Similarity	NPC218158
0.8387	Intermediate Similarity	NPC469403
0.8384	Intermediate Similarity	NPC471365
0.8384	Intermediate Similarity	NPC132395
0.8384	Intermediate Similarity	NPC471364
0.8352	Intermediate Similarity	NPC118266
0.8333	Intermediate Similarity	NPC471367
0.8298	Intermediate Similarity	NPC65513
0.828	Intermediate Similarity	NPC470819
0.8265	Intermediate Similarity	NPC228251
0.8265	Intermediate Similarity	NPC161527
0.8265	Intermediate Similarity	NPC477972
0.8265	Intermediate Similarity	NPC219285
0.8265	Intermediate Similarity	NPC477971
0.8265	Intermediate Similarity	NPC20113
0.8265	Intermediate Similarity	NPC477968
0.8252	Intermediate Similarity	NPC316708
0.8242	Intermediate Similarity	NPC472442
0.8222	Intermediate Similarity	NPC472440
0.8191	Intermediate Similarity	NPC470817
0.8191	Intermediate Similarity	NPC471370
0.8191	Intermediate Similarity	NPC471371
0.8173	Intermediate Similarity	NPC17791
0.8173	Intermediate Similarity	NPC470026
0.8172	Intermediate Similarity	NPC477128
0.8172	Intermediate Similarity	NPC69713
0.8155	Intermediate Similarity	NPC112457
0.8152	Intermediate Similarity	NPC471369
0.8152	Intermediate Similarity	NPC471368
0.8125	Intermediate Similarity	NPC477130
0.8125	Intermediate Similarity	NPC477722
0.8125	Intermediate Similarity	NPC477129
0.8095	Intermediate Similarity	NPC470025
0.8095	Intermediate Similarity	NPC328074
0.8095	Intermediate Similarity	NPC321272
0.8095	Intermediate Similarity	NPC317460
0.8085	Intermediate Similarity	NPC284561
0.8065	Intermediate Similarity	NPC102640
0.8061	Intermediate Similarity	NPC309503
0.8061	Intermediate Similarity	NPC96597
0.8061	Intermediate Similarity	NPC204054
0.8061	Intermediate Similarity	NPC155319
0.8061	Intermediate Similarity	NPC125551
0.8061	Intermediate Similarity	NPC239547
0.8061	Intermediate Similarity	NPC91197
0.8061	Intermediate Similarity	NPC257726
0.8043	Intermediate Similarity	NPC119001
0.8041	Intermediate Similarity	NPC286612
0.8041	Intermediate Similarity	NPC230347
0.8041	Intermediate Similarity	NPC275310
0.8021	Intermediate Similarity	NPC475657
0.8021	Intermediate Similarity	NPC471571
0.802	Intermediate Similarity	NPC120009
0.8019	Intermediate Similarity	NPC470027
0.8	Intermediate Similarity	NPC469595
0.8	Intermediate Similarity	NPC212679
0.8	Intermediate Similarity	NPC220454
0.798	Intermediate Similarity	NPC473154
0.7979	Intermediate Similarity	NPC196407
0.7979	Intermediate Similarity	NPC263079
0.7963	Intermediate Similarity	NPC23046
0.7959	Intermediate Similarity	NPC73858
0.7957	Intermediate Similarity	NPC244174
0.7957	Intermediate Similarity	NPC102996
0.7941	Intermediate Similarity	NPC222161
0.7921	Intermediate Similarity	NPC469606
0.7921	Intermediate Similarity	NPC273005
0.7921	Intermediate Similarity	NPC31058
0.7921	Intermediate Similarity	NPC471993
0.7917	Intermediate Similarity	NPC474631
0.7917	Intermediate Similarity	NPC477574
0.7889	Intermediate Similarity	NPC469802
0.7864	Intermediate Similarity	NPC82251
0.7857	Intermediate Similarity	NPC473369
0.7857	Intermediate Similarity	NPC135224
0.7857	Intermediate Similarity	NPC477970
0.7857	Intermediate Similarity	NPC477969
0.7857	Intermediate Similarity	NPC281134
0.7857	Intermediate Similarity	NPC100892
0.785	Intermediate Similarity	NPC157441
0.785	Intermediate Similarity	NPC293658
0.785	Intermediate Similarity	NPC474410
0.7835	Intermediate Similarity	NPC99653
0.7826	Intermediate Similarity	NPC469
0.7822	Intermediate Similarity	NPC280991
0.7812	Intermediate Similarity	NPC469372
0.78	Intermediate Similarity	NPC474440
0.7789	Intermediate Similarity	NPC473879
0.7788	Intermediate Similarity	NPC475074
0.7766	Intermediate Similarity	NPC323209
0.7757	Intermediate Similarity	NPC12046
0.7757	Intermediate Similarity	NPC194951
0.7755	Intermediate Similarity	NPC470255
0.7755	Intermediate Similarity	NPC189513
0.7755	Intermediate Similarity	NPC304968
0.7755	Intermediate Similarity	NPC104925
0.7755	Intermediate Similarity	NPC469491
0.7755	Intermediate Similarity	NPC128488
0.7755	Intermediate Similarity	NPC298973
0.7745	Intermediate Similarity	NPC134077
0.7742	Intermediate Similarity	NPC71626
0.7732	Intermediate Similarity	NPC234335
0.7732	Intermediate Similarity	NPC124374
0.7732	Intermediate Similarity	NPC179517
0.7732	Intermediate Similarity	NPC165904
0.7723	Intermediate Similarity	NPC324841
0.7723	Intermediate Similarity	NPC477716
0.7723	Intermediate Similarity	NPC477721
0.7723	Intermediate Similarity	NPC470761
0.7723	Intermediate Similarity	NPC473219
0.7723	Intermediate Similarity	NPC477720
0.7717	Intermediate Similarity	NPC471218
0.7708	Intermediate Similarity	NPC246028
0.7708	Intermediate Similarity	NPC177141
0.7708	Intermediate Similarity	NPC174765
0.7708	Intermediate Similarity	NPC470734
0.7708	Intermediate Similarity	NPC261320
0.7692	Intermediate Similarity	NPC127609
0.7692	Intermediate Similarity	NPC239961
0.7692	Intermediate Similarity	NPC233332
0.7692	Intermediate Similarity	NPC195424
0.7692	Intermediate Similarity	NPC127790
0.7692	Intermediate Similarity	NPC469607
0.7677	Intermediate Similarity	NPC37603
0.7677	Intermediate Similarity	NPC471786
0.7677	Intermediate Similarity	NPC13924
0.767	Intermediate Similarity	NPC471450
0.767	Intermediate Similarity	NPC45897
0.767	Intermediate Similarity	NPC23584
0.767	Intermediate Similarity	NPC254202
0.7658	Intermediate Similarity	NPC475834
0.7658	Intermediate Similarity	NPC474179
0.7653	Intermediate Similarity	NPC67398
0.7653	Intermediate Similarity	NPC91654
0.7653	Intermediate Similarity	NPC166346
0.7653	Intermediate Similarity	NPC163902
0.7653	Intermediate Similarity	NPC474792
0.7647	Intermediate Similarity	NPC298233
0.7647	Intermediate Similarity	NPC63249
0.7647	Intermediate Similarity	NPC473384
0.7647	Intermediate Similarity	NPC198992
0.7647	Intermediate Similarity	NPC477717
0.7642	Intermediate Similarity	NPC206618
0.7629	Intermediate Similarity	NPC48732
0.7629	Intermediate Similarity	NPC159876
0.7629	Intermediate Similarity	NPC328935
0.7629	Intermediate Similarity	NPC220216
0.7629	Intermediate Similarity	NPC327183
0.7619	Intermediate Similarity	NPC293512
0.7609	Intermediate Similarity	NPC25554
0.7604	Intermediate Similarity	NPC24816
0.7604	Intermediate Similarity	NPC106332
0.7604	Intermediate Similarity	NPC473151

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 NPC88507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1188
0.2-0.3	3836
0.3-0.4	2623
0.4-0.5	855
0.5-0.6	309
0.6-0.7	161
0.7-0.8	7
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
0.7547	Intermediate Similarity	NPD6686	Approved
0.7282	Intermediate Similarity	NPD7638	Approved
0.7217	Intermediate Similarity	NPD7503	Approved
0.7212	Intermediate Similarity	NPD7639	Approved
0.7212	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7637	Suspended
0.7172	Intermediate Similarity	NPD6051	Approved
0.7158	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8039	Approved
0.7115	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1694	Approved
0.701	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6412	Phase 2
0.6961	Remote Similarity	NPD5779	Approved
0.6961	Remote Similarity	NPD5778	Approved
0.6961	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD8515	Approved
0.6869	Remote Similarity	NPD7146	Approved
0.6869	Remote Similarity	NPD5330	Approved
0.6869	Remote Similarity	NPD6684	Approved
0.6869	Remote Similarity	NPD6409	Approved
0.6869	Remote Similarity	NPD7521	Approved
0.6869	Remote Similarity	NPD7334	Approved
0.681	Remote Similarity	NPD7327	Approved
0.681	Remote Similarity	NPD7328	Approved
0.6792	Remote Similarity	NPD4225	Approved
0.6782	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8033	Approved
0.6765	Remote Similarity	NPD7838	Discovery
0.6752	Remote Similarity	NPD7516	Approved
0.6733	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6903	Approved
0.6733	Remote Similarity	NPD5737	Approved
0.6733	Remote Similarity	NPD6672	Approved
0.6729	Remote Similarity	NPD6648	Approved
0.6727	Remote Similarity	NPD6008	Approved
0.6699	Remote Similarity	NPD6411	Approved
0.6695	Remote Similarity	NPD8377	Approved
0.6695	Remote Similarity	NPD8294	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8335	Approved
0.6639	Remote Similarity	NPD8380	Approved
0.6639	Remote Similarity	NPD8296	Approved
0.6639	Remote Similarity	NPD8379	Approved
0.6639	Remote Similarity	NPD8378	Approved
0.6633	Remote Similarity	NPD5209	Approved
0.6609	Remote Similarity	NPD8133	Approved
0.6606	Remote Similarity	NPD7632	Discontinued
0.6602	Remote Similarity	NPD5207	Approved
0.6579	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7900	Approved
0.6571	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6695	Phase 3
0.6549	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5694	Approved
0.6538	Remote Similarity	NPD5693	Phase 1
0.6538	Remote Similarity	NPD6050	Approved
0.6532	Remote Similarity	NPD7319	Approved
0.6522	Remote Similarity	NPD6053	Discontinued
0.6518	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD4251	Approved
0.6452	Remote Similarity	NPD7736	Approved
0.6446	Remote Similarity	NPD6370	Approved
0.6442	Remote Similarity	NPD5692	Phase 3
0.6442	Remote Similarity	NPD46	Approved
0.6442	Remote Similarity	NPD6698	Approved
0.6415	Remote Similarity	NPD7748	Approved
0.6404	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7902	Approved
0.6381	Remote Similarity	NPD5284	Approved
0.6381	Remote Similarity	NPD7983	Approved
0.6381	Remote Similarity	NPD5281	Approved
0.6379	Remote Similarity	NPD6882	Approved
0.6373	Remote Similarity	NPD6098	Approved
0.6373	Remote Similarity	NPD4249	Approved
0.6371	Remote Similarity	NPD8293	Discontinued
0.6371	Remote Similarity	NPD8074	Phase 3
0.6364	Remote Similarity	NPD5344	Discontinued
0.6355	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1695	Approved
0.6346	Remote Similarity	NPD6904	Approved
0.6346	Remote Similarity	NPD6080	Approved
0.6346	Remote Similarity	NPD6673	Approved
0.6341	Remote Similarity	NPD7492	Approved
0.6337	Remote Similarity	NPD4786	Approved
0.6337	Remote Similarity	NPD3668	Phase 3
0.6327	Remote Similarity	NPD6929	Approved
0.6311	Remote Similarity	NPD7750	Discontinued
0.6311	Remote Similarity	NPD7524	Approved
0.6303	Remote Similarity	NPD6009	Approved
0.6303	Remote Similarity	NPD7115	Discovery
0.6303	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3667	Approved
0.6299	Remote Similarity	NPD7260	Phase 2
0.6296	Remote Similarity	NPD7839	Suspended
0.629	Remote Similarity	NPD6616	Approved
0.6281	Remote Similarity	NPD6054	Approved
0.6275	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6930	Phase 2
0.6263	Remote Similarity	NPD6931	Approved
0.6263	Remote Similarity	NPD7332	Phase 2
0.6263	Remote Similarity	NPD7514	Phase 3
0.6263	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8328	Phase 3
0.626	Remote Similarity	NPD6067	Discontinued
0.625	Remote Similarity	NPD8264	Approved
0.624	Remote Similarity	NPD7078	Approved
0.6239	Remote Similarity	NPD6083	Phase 2
0.6239	Remote Similarity	NPD6084	Phase 2
0.6226	Remote Similarity	NPD7515	Phase 2
0.6224	Remote Similarity	NPD7145	Approved
0.6204	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5695	Phase 3
0.62	Remote Similarity	NPD6902	Approved
0.619	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6881	Approved
0.6174	Remote Similarity	NPD6899	Approved
0.6154	Remote Similarity	NPD3573	Approved
0.6148	Remote Similarity	NPD6059	Approved
0.6146	Remote Similarity	NPD6926	Approved
0.6146	Remote Similarity	NPD6924	Approved
0.614	Remote Similarity	NPD7128	Approved
0.614	Remote Similarity	NPD6402	Approved
0.614	Remote Similarity	NPD6675	Approved
0.614	Remote Similarity	NPD5739	Approved
0.6132	Remote Similarity	NPD5785	Approved
0.6122	Remote Similarity	NPD6925	Approved
0.6122	Remote Similarity	NPD6932	Approved
0.6122	Remote Similarity	NPD5776	Phase 2
0.6117	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5282	Discontinued
0.61	Remote Similarity	NPD4819	Approved
0.61	Remote Similarity	NPD4820	Approved
0.61	Remote Similarity	NPD4822	Approved
0.61	Remote Similarity	NPD4821	Approved
0.6098	Remote Similarity	NPD6016	Approved
0.6098	Remote Similarity	NPD6015	Approved
0.6095	Remote Similarity	NPD5208	Approved
0.6087	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5697	Approved
0.6082	Remote Similarity	NPD7339	Approved
0.6082	Remote Similarity	NPD6942	Approved
0.6078	Remote Similarity	NPD7154	Phase 3
0.6078	Remote Similarity	NPD5362	Discontinued
0.6075	Remote Similarity	NPD8034	Phase 2
0.6075	Remote Similarity	NPD8035	Phase 2
0.6075	Remote Similarity	NPD7087	Discontinued
0.6068	Remote Similarity	NPD6883	Approved
0.6068	Remote Similarity	NPD7290	Approved
0.6068	Remote Similarity	NPD7102	Approved
0.6068	Remote Similarity	NPD6371	Approved
0.6061	Remote Similarity	NPD4271	Approved
0.6061	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4268	Approved
0.6061	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5279	Phase 3
0.6055	Remote Similarity	NPD5654	Approved
0.605	Remote Similarity	NPD4632	Approved
0.6048	Remote Similarity	NPD5988	Approved
0.6036	Remote Similarity	NPD5696	Approved
0.6034	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6011	Approved
0.6034	Remote Similarity	NPD7320	Approved
0.6032	Remote Similarity	NPD8451	Approved
0.602	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6933	Approved
0.6019	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD3665	Phase 1
0.6017	Remote Similarity	NPD6650	Approved
0.6017	Remote Similarity	NPD8130	Phase 1
0.6017	Remote Similarity	NPD6869	Approved
0.6017	Remote Similarity	NPD6847	Approved
0.6017	Remote Similarity	NPD6649	Approved
0.6017	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7144	Approved
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD7143	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD7122	Discontinued
0.5984	Remote Similarity	NPD8448	Approved
0.5983	Remote Similarity	NPD6372	Approved
0.5983	Remote Similarity	NPD6012	Approved
0.5983	Remote Similarity	NPD6014	Approved
0.5983	Remote Similarity	NPD6013	Approved
0.5983	Remote Similarity	NPD6373	Approved
0.5978	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6914	Discontinued
0.5968	Remote Similarity	NPD8444	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