NPASS Compound

Structure

NPC471371 OpenBabel07101718332D 32 34 0 0 1 0 0 0 0 0999 V2000 3.2954 -1.0763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7364 1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7649 2.7343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6919 -0.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6160 -2.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3364 1.8930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3452 -1.2783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7649 1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6951 -0.5564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3078 1.8930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0094 -0.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8221 1.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1681 0.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3268 2.5089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0094 2.5089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2792 1.8930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8506 0.0803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9659 -2.2662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1681 2.9946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3268 1.5375 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0094 1.5375 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9953 0.3675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3951 0.8874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9661 0.1015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8506 1.0517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1681 1.0517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0157 -2.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1681 3.9660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9455 0.5695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2661 -1.3423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3453 1.0894 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 7 1 0 0 0 0 2 8 2 0 0 0 0 3 16 2 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 7 9 1 0 0 0 0 8 16 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 25 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 17 25 1 6 0 0 0 18 27 2 0 0 0 0 18 30 1 0 0 0 0 19 28 1 6 0 0 0 20 23 1 0 0 0 0 20 26 1 6 0 0 0 21 25 1 1 0 0 0 21 26 1 0 0 0 0 22 29 2 0 0 0 0 22 31 1 0 0 0 0 23 31 1 6 0 0 0 23 32 1 0 0 0 0 24 26 1 6 0 0 0 24 30 1 0 0 0 0 24 32 1 0 0 0 0 25 6 1 1 0 0 0 26 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.28
Volume:	474.778
LogP:	4.184
LogD:	3.785
LogS:	-4.916
# Rotatable Bonds:	10
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	5.596
Fsp3:	0.769
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:	-4.744
MDCK Permeability:	1.9311486539663747e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.393
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.344
Plasma Protein Binding (PPB):	71.01205444335938%
Volume Distribution (VD):	1.34
Pgp-substrate:	33.22643280029297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.464
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.669
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	5.826
Half-life (T1/2):	0.444

ADMET: Toxicity

hERG Blockers:	0.193
Human Hepatotoxicity (H-HT):	0.751
Drug-inuced Liver Injury (DILI):	0.503
AMES Toxicity:	0.713
Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.949
Carcinogencity:	0.719
Eye Corrosion:	0.062
Eye Irritation:	0.051
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC471371

Natural Product ID:	NPC471371
*Common Name:**	2-Epicaseabalansin B
IUPAC Name:	[(1R,3S,3aS,5S,6aR,7S,8S,10aR)-1-acetyloxy-5-hydroxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,3a,4,5,6,6a,8,9,10-decahydrobenzo[d][2]benzofuran-3-yl] butanoate
Synonyms:
Standard InCHIKey:	PPMBXKDPXYHOGH-CZROZBDGSA-N
Standard InCHI:	InChI=1S/C26H40O6/c1-7-9-22(29)31-23-20-14-19(28)15-21-25(6,12-10-16(3)8-2)17(4)11-13-26(20,21)24(32-23)30-18(5)27/h8,17,19-21,23-24,28H,2-3,7,9-15H2,1,4-6H3/t17-,19+,20+,21+,23+,24-,25-,26-/m0/s1
SMILES:	CCCC(=O)OC1C2CC(CC3C2(CCC(C3(C)CCC(=C)C=C)C)C(O1)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419881
PubChem CID:	73349186
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
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[24033131]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	twigs	n.a.	n.a.	PMID[25286284]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26699618]

☑ 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	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	58100.0	nM	PMID[570152]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	13900.0	nM	PMID[570152]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	25300.0	nM	PMID[570152]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	67200.0	nM	PMID[570152]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	7200.0	nM	PMID[570152]

☑ 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 NPC471371 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	170
0.1-0.2	1189
0.2-0.3	5078
0.3-0.4	13819
0.4-0.5	8620
0.5-0.6	5689
0.6-0.7	6425
0.7-0.8	1615
0.8-0.85	83
0.85-0.9	5
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471370
0.9762	High Similarity	NPC263079
0.9286	High Similarity	NPC471367
0.907	High Similarity	NPC471369
0.8851	High Similarity	NPC471368
0.8737	High Similarity	NPC471363
0.8737	High Similarity	NPC238397
0.8646	High Similarity	NPC7613
0.8646	High Similarity	NPC7644
0.8646	High Similarity	NPC134270
0.8646	High Similarity	NPC127933
0.8646	High Similarity	NPC475889
0.8557	High Similarity	NPC470321
0.8557	High Similarity	NPC201880
0.8557	High Similarity	NPC473207
0.8557	High Similarity	NPC81567
0.8557	High Similarity	NPC264867
0.8469	Intermediate Similarity	NPC218158
0.8469	Intermediate Similarity	NPC252296
0.8384	Intermediate Similarity	NPC184512
0.8384	Intermediate Similarity	NPC88013
0.8384	Intermediate Similarity	NPC125423
0.8316	Intermediate Similarity	NPC472188
0.8316	Intermediate Similarity	NPC471770
0.8316	Intermediate Similarity	NPC278939
0.8316	Intermediate Similarity	NPC473555
0.8316	Intermediate Similarity	NPC98112
0.83	Intermediate Similarity	NPC48548
0.83	Intermediate Similarity	NPC311223
0.83	Intermediate Similarity	NPC135015
0.83	Intermediate Similarity	NPC128795
0.83	Intermediate Similarity	NPC217921
0.8298	Intermediate Similarity	NPC275310
0.8298	Intermediate Similarity	NPC286612
0.8298	Intermediate Similarity	NPC230347
0.8229	Intermediate Similarity	NPC157739
0.8229	Intermediate Similarity	NPC476800
0.8229	Intermediate Similarity	NPC318917
0.8229	Intermediate Similarity	NPC471366
0.8229	Intermediate Similarity	NPC472186
0.8218	Intermediate Similarity	NPC40728
0.8218	Intermediate Similarity	NPC316974
0.8191	Intermediate Similarity	NPC211238
0.8191	Intermediate Similarity	NPC88507
0.8144	Intermediate Similarity	NPC161527
0.8144	Intermediate Similarity	NPC228251
0.8144	Intermediate Similarity	NPC477972
0.8144	Intermediate Similarity	NPC219285
0.8144	Intermediate Similarity	NPC477971
0.8144	Intermediate Similarity	NPC473204
0.8144	Intermediate Similarity	NPC317019
0.8144	Intermediate Similarity	NPC473545
0.8144	Intermediate Similarity	NPC472187
0.8144	Intermediate Similarity	NPC20113
0.8144	Intermediate Similarity	NPC477968
0.8137	Intermediate Similarity	NPC119550
0.8125	Intermediate Similarity	NPC97867
0.8111	Intermediate Similarity	NPC164424
0.8105	Intermediate Similarity	NPC472189
0.8105	Intermediate Similarity	NPC471362
0.8105	Intermediate Similarity	NPC471372
0.81	Intermediate Similarity	NPC172867
0.8085	Intermediate Similarity	NPC474835
0.8085	Intermediate Similarity	NPC12297
0.8041	Intermediate Similarity	NPC473154
0.8021	Intermediate Similarity	NPC171598
0.8021	Intermediate Similarity	NPC311166
0.802	Intermediate Similarity	NPC293512
0.802	Intermediate Similarity	NPC109376
0.8	Intermediate Similarity	NPC31430
0.8	Intermediate Similarity	NPC102048
0.8	Intermediate Similarity	NPC299963
0.8	Intermediate Similarity	NPC97505
0.8	Intermediate Similarity	NPC85593
0.798	Intermediate Similarity	NPC154452
0.798	Intermediate Similarity	NPC470571
0.7979	Intermediate Similarity	NPC120539
0.7978	Intermediate Similarity	NPC472504
0.7961	Intermediate Similarity	NPC86217
0.7961	Intermediate Similarity	NPC101450
0.7959	Intermediate Similarity	NPC324841
0.7959	Intermediate Similarity	NPC146188
0.7957	Intermediate Similarity	NPC473058
0.7941	Intermediate Similarity	NPC224660
0.7941	Intermediate Similarity	NPC470024
0.7941	Intermediate Similarity	NPC230888
0.7921	Intermediate Similarity	NPC470055
0.7921	Intermediate Similarity	NPC470056
0.7912	Intermediate Similarity	NPC476602
0.79	Intermediate Similarity	NPC120009
0.7895	Intermediate Similarity	NPC246860
0.7895	Intermediate Similarity	NPC267266
0.7895	Intermediate Similarity	NPC470656
0.7895	Intermediate Similarity	NPC277721
0.7889	Intermediate Similarity	NPC474284
0.7889	Intermediate Similarity	NPC474253
0.7889	Intermediate Similarity	NPC213737
0.7889	Intermediate Similarity	NPC475820
0.7889	Intermediate Similarity	NPC474346
0.7879	Intermediate Similarity	NPC21064
0.7879	Intermediate Similarity	NPC121072
0.7872	Intermediate Similarity	NPC153853
0.7872	Intermediate Similarity	NPC469403
0.7872	Intermediate Similarity	NPC159876
0.7864	Intermediate Similarity	NPC471250
0.7864	Intermediate Similarity	NPC305939
0.7857	Intermediate Similarity	NPC477928
0.7843	Intermediate Similarity	NPC475074
0.7835	Intermediate Similarity	NPC94905
0.7835	Intermediate Similarity	NPC8954
0.7822	Intermediate Similarity	NPC470062
0.7822	Intermediate Similarity	NPC470061
0.7822	Intermediate Similarity	NPC470057
0.7822	Intermediate Similarity	NPC470064
0.7822	Intermediate Similarity	NPC470058
0.7822	Intermediate Similarity	NPC470059
0.7822	Intermediate Similarity	NPC470043
0.7822	Intermediate Similarity	NPC470060
0.7822	Intermediate Similarity	NPC222161
0.7812	Intermediate Similarity	NPC96736
0.7812	Intermediate Similarity	NPC305160
0.7812	Intermediate Similarity	NPC178949
0.78	Intermediate Similarity	NPC94919
0.7789	Intermediate Similarity	NPC48463
0.7788	Intermediate Similarity	NPC316708
0.7778	Intermediate Similarity	NPC2096
0.7778	Intermediate Similarity	NPC208912
0.7767	Intermediate Similarity	NPC295389
0.7767	Intermediate Similarity	NPC469845
0.7767	Intermediate Similarity	NPC88744
0.7766	Intermediate Similarity	NPC470819
0.7766	Intermediate Similarity	NPC16265
0.7766	Intermediate Similarity	NPC194642
0.7755	Intermediate Similarity	NPC253586
0.7755	Intermediate Similarity	NPC198549
0.7755	Intermediate Similarity	NPC239547
0.7755	Intermediate Similarity	NPC309503
0.7755	Intermediate Similarity	NPC155319
0.7755	Intermediate Similarity	NPC91197
0.7755	Intermediate Similarity	NPC96597
0.7755	Intermediate Similarity	NPC125551
0.7755	Intermediate Similarity	NPC113976
0.7745	Intermediate Similarity	NPC285927
0.7745	Intermediate Similarity	NPC103172
0.7745	Intermediate Similarity	NPC164600
0.7745	Intermediate Similarity	NPC239961
0.7745	Intermediate Similarity	NPC473199
0.7736	Intermediate Similarity	NPC157441
0.7732	Intermediate Similarity	NPC259042
0.7732	Intermediate Similarity	NPC477970
0.7732	Intermediate Similarity	NPC477969
0.7732	Intermediate Similarity	NPC100892
0.7732	Intermediate Similarity	NPC157686
0.7732	Intermediate Similarity	NPC135224
0.7717	Intermediate Similarity	NPC235402
0.7717	Intermediate Similarity	NPC329738
0.7714	Intermediate Similarity	NPC285410
0.7714	Intermediate Similarity	NPC263827
0.7714	Intermediate Similarity	NPC17791
0.7714	Intermediate Similarity	NPC272242
0.7714	Intermediate Similarity	NPC471251
0.7714	Intermediate Similarity	NPC470026
0.7714	Intermediate Similarity	NPC250481
0.7708	Intermediate Similarity	NPC163902
0.7708	Intermediate Similarity	NPC199543
0.7708	Intermediate Similarity	NPC147272
0.77	Intermediate Similarity	NPC198992
0.7692	Intermediate Similarity	NPC204407
0.7692	Intermediate Similarity	NPC52108
0.7692	Intermediate Similarity	NPC51947
0.7692	Intermediate Similarity	NPC91583
0.7692	Intermediate Similarity	NPC237503
0.7692	Intermediate Similarity	NPC474789
0.7692	Intermediate Similarity	NPC137917
0.7692	Intermediate Similarity	NPC240125
0.7692	Intermediate Similarity	NPC306746
0.7692	Intermediate Similarity	NPC57362
0.7692	Intermediate Similarity	NPC206618
0.7692	Intermediate Similarity	NPC167383
0.7692	Intermediate Similarity	NPC473844
0.7684	Intermediate Similarity	NPC470817
0.7684	Intermediate Similarity	NPC53890
0.7684	Intermediate Similarity	NPC123252
0.7684	Intermediate Similarity	NPC10274
0.7684	Intermediate Similarity	NPC474249
0.7684	Intermediate Similarity	NPC219937
0.7684	Intermediate Similarity	NPC194485
0.7684	Intermediate Similarity	NPC261990
0.7684	Intermediate Similarity	NPC48732
0.7684	Intermediate Similarity	NPC232202
0.7677	Intermediate Similarity	NPC5358
0.7677	Intermediate Similarity	NPC216260
0.7677	Intermediate Similarity	NPC474440
0.767	Intermediate Similarity	NPC473538
0.767	Intermediate Similarity	NPC88833
0.767	Intermediate Similarity	NPC61071
0.767	Intermediate Similarity	NPC283849
0.767	Intermediate Similarity	NPC96333
0.767	Intermediate Similarity	NPC234160
0.7667	Intermediate Similarity	NPC209318

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 NPC471371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1546
0.2-0.3	4150
0.3-0.4	2230
0.4-0.5	575
0.5-0.6	244
0.6-0.7	241
0.7-0.8	16
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
0.75	Intermediate Similarity	NPD7638	Approved
0.7429	Intermediate Similarity	NPD6686	Approved
0.7426	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD7640	Approved
0.7407	Intermediate Similarity	NPD8133	Approved
0.7333	Intermediate Similarity	NPD6412	Phase 2
0.7245	Intermediate Similarity	NPD8035	Phase 2
0.7245	Intermediate Similarity	NPD8034	Phase 2
0.7196	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6399	Phase 3
0.7158	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7637	Suspended
0.7043	Intermediate Similarity	NPD6370	Approved
0.7034	Intermediate Similarity	NPD7736	Approved
0.7	Intermediate Similarity	NPD6882	Approved
0.6991	Remote Similarity	NPD7327	Approved
0.6991	Remote Similarity	NPD7328	Approved
0.6957	Remote Similarity	NPD7503	Approved
0.6949	Remote Similarity	NPD8293	Discontinued
0.6931	Remote Similarity	NPD7748	Approved
0.693	Remote Similarity	NPD7516	Approved
0.6923	Remote Similarity	NPD7492	Approved
0.6903	Remote Similarity	NPD6009	Approved
0.69	Remote Similarity	NPD7515	Phase 2
0.6893	Remote Similarity	NPD7902	Approved
0.687	Remote Similarity	NPD8377	Approved
0.687	Remote Similarity	NPD8294	Approved
0.687	Remote Similarity	NPD6054	Approved
0.6864	Remote Similarity	NPD7507	Approved
0.6864	Remote Similarity	NPD6616	Approved
0.6838	Remote Similarity	NPD6067	Discontinued
0.6838	Remote Similarity	NPD8328	Phase 3
0.6827	Remote Similarity	NPD4225	Approved
0.681	Remote Similarity	NPD8379	Approved
0.681	Remote Similarity	NPD8296	Approved
0.681	Remote Similarity	NPD8033	Approved
0.681	Remote Similarity	NPD8378	Approved
0.681	Remote Similarity	NPD8380	Approved
0.681	Remote Similarity	NPD8335	Approved
0.6809	Remote Similarity	NPD7525	Registered
0.6809	Remote Similarity	NPD6928	Phase 2
0.6807	Remote Similarity	NPD7078	Approved
0.6792	Remote Similarity	NPD7632	Discontinued
0.6789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6881	Approved
0.6789	Remote Similarity	NPD6899	Approved
0.6774	Remote Similarity	NPD6118	Approved
0.6774	Remote Similarity	NPD6114	Approved
0.6774	Remote Similarity	NPD6115	Approved
0.6774	Remote Similarity	NPD6697	Approved
0.6759	Remote Similarity	NPD7128	Approved
0.6759	Remote Similarity	NPD5739	Approved
0.6759	Remote Similarity	NPD6675	Approved
0.6759	Remote Similarity	NPD6402	Approved
0.6754	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6411	Approved
0.6724	Remote Similarity	NPD6059	Approved
0.6701	Remote Similarity	NPD4786	Approved
0.6701	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5697	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6637	Remote Similarity	NPD4632	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.661	Remote Similarity	NPD5988	Approved
0.6607	Remote Similarity	NPD6847	Approved
0.6607	Remote Similarity	NPD6650	Approved
0.6607	Remote Similarity	NPD8130	Phase 1
0.6607	Remote Similarity	NPD6617	Approved
0.6607	Remote Similarity	NPD6869	Approved
0.6607	Remote Similarity	NPD6649	Approved
0.6606	Remote Similarity	NPD6008	Approved
0.6602	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7900	Approved
0.6598	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3669	Approved
0.6598	Remote Similarity	NPD6695	Phase 3
0.6577	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6577	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD6372	Approved
0.6577	Remote Similarity	NPD6013	Approved
0.6571	Remote Similarity	NPD6084	Phase 2
0.6571	Remote Similarity	NPD6083	Phase 2
0.6569	Remote Similarity	NPD6079	Approved
0.6566	Remote Similarity	NPD6409	Approved
0.6566	Remote Similarity	NPD6684	Approved
0.6566	Remote Similarity	NPD5330	Approved
0.6566	Remote Similarity	NPD7521	Approved
0.6566	Remote Similarity	NPD7146	Approved
0.6566	Remote Similarity	NPD3618	Phase 1
0.6566	Remote Similarity	NPD7334	Approved
0.6559	Remote Similarity	NPD6117	Approved
0.6549	Remote Similarity	NPD8297	Approved
0.6545	Remote Similarity	NPD5701	Approved
0.6535	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6101	Approved
0.6535	Remote Similarity	NPD5328	Approved
0.6526	Remote Similarity	NPD7645	Phase 2
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8515	Approved
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.6522	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD8171	Discontinued
0.646	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7339	Approved
0.6452	Remote Similarity	NPD6942	Approved
0.6441	Remote Similarity	NPD6319	Approved
0.6436	Remote Similarity	NPD6672	Approved
0.6436	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7604	Phase 2
0.6387	Remote Similarity	NPD5983	Phase 2
0.6383	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6354	Remote Similarity	NPD6929	Approved
0.6346	Remote Similarity	NPD4202	Approved
0.6344	Remote Similarity	NPD6926	Approved
0.6344	Remote Similarity	NPD6924	Approved
0.6341	Remote Similarity	NPD6033	Approved
0.6337	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD7524	Approved
0.6337	Remote Similarity	NPD7750	Discontinued
0.6337	Remote Similarity	NPD4251	Approved
0.6327	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5221	Approved
0.6321	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5222	Approved
0.6316	Remote Similarity	NPD6932	Approved
0.6311	Remote Similarity	NPD6336	Discontinued
0.6304	Remote Similarity	NPD7152	Approved
0.6304	Remote Similarity	NPD7150	Approved
0.6304	Remote Similarity	NPD7151	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.6289	Remote Similarity	NPD6930	Phase 2
0.6289	Remote Similarity	NPD6931	Approved
0.6289	Remote Similarity	NPD7509	Discontinued
0.6271	Remote Similarity	NPD6335	Approved
0.6263	Remote Similarity	NPD4788	Approved
0.6262	Remote Similarity	NPD4755	Approved
0.6262	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD7145	Approved
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD5281	Approved
0.6239	Remote Similarity	NPD5344	Discontinued
0.6239	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD6868	Approved
0.6238	Remote Similarity	NPD4249	Approved
0.6228	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5695	Phase 3
0.6218	Remote Similarity	NPD7101	Approved
0.6218	Remote Similarity	NPD7100	Approved
0.6214	Remote Similarity	NPD6051	Approved
0.6211	Remote Similarity	NPD6933	Approved
0.6204	Remote Similarity	NPD5696	Approved
0.62	Remote Similarity	NPD3668	Phase 3
0.6196	Remote Similarity	NPD7144	Approved
0.6196	Remote Similarity	NPD7143	Approved
0.6186	Remote Similarity	NPD7115	Discovery
0.6186	Remote Similarity	NPD6317	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.6182	Remote Similarity	NPD5211	Phase 2
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.6176	Remote Similarity	NPD3573	Approved
0.6174	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1811	Approved
0.617	Remote Similarity	NPD1810	Approved
0.6168	Remote Similarity	NPD4697	Phase 3
0.6162	Remote Similarity	NPD6435	Approved
0.6154	Remote Similarity	NPD7838	Discovery
0.6147	Remote Similarity	NPD6648	Approved
0.6147	Remote Similarity	NPD4700	Approved
0.6146	Remote Similarity	NPD6925	Approved
0.6146	Remote Similarity	NPD5776	Phase 2
0.6139	Remote Similarity	NPD1694	Approved
0.6134	Remote Similarity	NPD6313	Approved
0.6134	Remote Similarity	NPD6314	Approved
0.6132	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