NPASS Compound

Structure

NPC247877 OpenBabel07101718292D 29 33 0 0 1 0 0 0 0 0999 V2000 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3690 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3690 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8690 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0029 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7350 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 5 1 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 22 1 0 0 0 0 9 28 1 0 0 0 0 10 1 1 1 0 0 0 10 29 1 0 0 0 0 11 4 1 6 0 0 0 11 22 1 0 0 0 0 12 6 1 6 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 21 1 1 0 0 0 14 21 1 0 0 0 0 14 23 2 0 0 0 0 15 7 1 6 0 0 0 15 20 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 24 2 0 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 19 22 1 0 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 21 9 1 1 0 0 0 22 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.2
Volume:	399.908
LogP:	2.25
LogD:	1.022
LogS:	-2.752
# Rotatable Bonds:	1
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	6.472
Fsp3:	0.864
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:	-5.26
MDCK Permeability:	7.823071791790426e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.649
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.83
Plasma Protein Binding (PPB):	60.07417297363281%
Volume Distribution (VD):	0.778
Pgp-substrate:	41.68094253540039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.411

ADMET: Excretion

Clearance (CL):	6.144
Half-life (T1/2):	0.286

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.535
Drug-inuced Liver Injury (DILI):	0.692
AMES Toxicity:	0.395
Rat Oral Acute Toxicity:	0.949
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.243
Carcinogencity:	0.591
Eye Corrosion:	0.087
Eye Irritation:	0.023
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC247877

Natural Product ID:	NPC247877
*Common Name:**	Laxiflorolide B
IUPAC Name:	n.a.
Synonyms:	Laxiflorolide B
Standard InCHIKey:	LEZIAYCXBOCYGM-LZZJPEJGSA-N
Standard InCHI:	InChI=1S/C22H30O7/c1-10-8-22(27,19(26)29-10)11-4-5-13-12(6-11)16(24)17(25)18-20(2,3)15-7-14(23)21(13,18)9-28-15/h10-13,15,17-18,25,27H,4-9H2,1-3H3/t10-,11-,12-,13-,15-,17-,18-,21-,22+/m1/s1
SMILES:	C[C@H]1OC(=O)[C@@](C1)(O)[C@@H]1CC[C@@H]2[C@@H](C1)C(=O)[C@H]([C@H]1[C@@]32CO[C@H](CC3=O)C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088262
PubChem CID:	60154783
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	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	10

Activity Type	# Activity
Cell Line	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[513902]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[513902]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[513902]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[513902]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[513902]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	39810.72	nM	PMID[513902]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	39810.72	nM	PMID[513902]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	39810.72	nM	PMID[513902]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	39810.72	nM	PMID[513902]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	39810.72	nM	PMID[513902]

☑ 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 NPC247877 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	474
0.1-0.2	3511
0.2-0.3	9010
0.3-0.4	13528
0.4-0.5	6771
0.5-0.6	4839
0.6-0.7	3386
0.7-0.8	1054
0.8-0.85	99
0.85-0.9	18
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC309127
0.9195	High Similarity	NPC120395
0.8764	High Similarity	NPC248216
0.8632	High Similarity	NPC74466
0.8632	High Similarity	NPC470632
0.8602	High Similarity	NPC472148
0.8602	High Similarity	NPC472147
0.8571	High Similarity	NPC236459
0.8462	Intermediate Similarity	NPC470920
0.8404	Intermediate Similarity	NPC474379
0.837	Intermediate Similarity	NPC90676
0.8316	Intermediate Similarity	NPC206878
0.828	Intermediate Similarity	NPC67653
0.828	Intermediate Similarity	NPC477440
0.828	Intermediate Similarity	NPC477443
0.828	Intermediate Similarity	NPC471459
0.8242	Intermediate Similarity	NPC62572
0.8191	Intermediate Similarity	NPC477433
0.8191	Intermediate Similarity	NPC477442
0.8191	Intermediate Similarity	NPC477444
0.8191	Intermediate Similarity	NPC472146
0.8191	Intermediate Similarity	NPC185529
0.8152	Intermediate Similarity	NPC92139
0.8132	Intermediate Similarity	NPC477434
0.8132	Intermediate Similarity	NPC79308
0.8132	Intermediate Similarity	NPC34984
0.8132	Intermediate Similarity	NPC25037
0.81	Intermediate Similarity	NPC471254
0.8041	Intermediate Similarity	NPC287354
0.8041	Intermediate Similarity	NPC62407
0.802	Intermediate Similarity	NPC471253
0.798	Intermediate Similarity	NPC253995
0.798	Intermediate Similarity	NPC474724
0.7979	Intermediate Similarity	NPC471221
0.7963	Intermediate Similarity	NPC470778
0.7963	Intermediate Similarity	NPC146432
0.7959	Intermediate Similarity	NPC235109
0.7959	Intermediate Similarity	NPC163685
0.7959	Intermediate Similarity	NPC477264
0.7959	Intermediate Similarity	NPC116683
0.7959	Intermediate Similarity	NPC223169
0.7957	Intermediate Similarity	NPC83242
0.7955	Intermediate Similarity	NPC307865
0.7944	Intermediate Similarity	NPC45218
0.7944	Intermediate Similarity	NPC268238
0.7944	Intermediate Similarity	NPC143268
0.7944	Intermediate Similarity	NPC299849
0.7944	Intermediate Similarity	NPC323821
0.7935	Intermediate Similarity	NPC105895
0.7935	Intermediate Similarity	NPC473299
0.7935	Intermediate Similarity	NPC237938
0.7935	Intermediate Similarity	NPC219535
0.7921	Intermediate Similarity	NPC470172
0.7917	Intermediate Similarity	NPC216137
0.7905	Intermediate Similarity	NPC470622
0.79	Intermediate Similarity	NPC80417
0.7895	Intermediate Similarity	NPC200580
0.7879	Intermediate Similarity	NPC471241
0.787	Intermediate Similarity	NPC190185
0.787	Intermediate Similarity	NPC89929
0.787	Intermediate Similarity	NPC16081
0.787	Intermediate Similarity	NPC213084
0.787	Intermediate Similarity	NPC173686
0.7857	Intermediate Similarity	NPC470031
0.7857	Intermediate Similarity	NPC82633
0.7849	Intermediate Similarity	NPC477445
0.7849	Intermediate Similarity	NPC477205
0.7843	Intermediate Similarity	NPC473406
0.7835	Intermediate Similarity	NPC476189
0.783	Intermediate Similarity	NPC473062
0.7822	Intermediate Similarity	NPC178853
0.7812	Intermediate Similarity	NPC475211
0.7812	Intermediate Similarity	NPC88337
0.7802	Intermediate Similarity	NPC280781
0.7802	Intermediate Similarity	NPC50658
0.7802	Intermediate Similarity	NPC48756
0.78	Intermediate Similarity	NPC109059
0.78	Intermediate Similarity	NPC472144
0.78	Intermediate Similarity	NPC288
0.7789	Intermediate Similarity	NPC131104
0.7789	Intermediate Similarity	NPC473319
0.7789	Intermediate Similarity	NPC3032
0.7789	Intermediate Similarity	NPC476435
0.7788	Intermediate Similarity	NPC203974
0.7778	Intermediate Similarity	NPC475785
0.7778	Intermediate Similarity	NPC275243
0.7778	Intermediate Similarity	NPC193785
0.7778	Intermediate Similarity	NPC165616
0.7767	Intermediate Similarity	NPC88469
0.7766	Intermediate Similarity	NPC80700
0.7766	Intermediate Similarity	NPC476717
0.7766	Intermediate Similarity	NPC477441
0.7757	Intermediate Similarity	NPC40608
0.7745	Intermediate Similarity	NPC80640
0.7742	Intermediate Similarity	NPC475689
0.7727	Intermediate Similarity	NPC17772
0.7723	Intermediate Similarity	NPC477655
0.7717	Intermediate Similarity	NPC289486
0.7717	Intermediate Similarity	NPC30583
0.7717	Intermediate Similarity	NPC61107
0.7714	Intermediate Similarity	NPC63841
0.7714	Intermediate Similarity	NPC208461
0.7714	Intermediate Similarity	NPC289702
0.7708	Intermediate Similarity	NPC253618
0.7708	Intermediate Similarity	NPC56962
0.7708	Intermediate Similarity	NPC24705
0.7708	Intermediate Similarity	NPC77001
0.7708	Intermediate Similarity	NPC61688
0.7706	Intermediate Similarity	NPC475490
0.7701	Intermediate Similarity	NPC474755
0.77	Intermediate Similarity	NPC472273
0.77	Intermediate Similarity	NPC472145
0.7692	Intermediate Similarity	NPC125366
0.7692	Intermediate Similarity	NPC181357
0.7692	Intermediate Similarity	NPC470587
0.7685	Intermediate Similarity	NPC94509
0.7684	Intermediate Similarity	NPC263802
0.7679	Intermediate Similarity	NPC470779
0.767	Intermediate Similarity	NPC107385
0.766	Intermediate Similarity	NPC473350
0.766	Intermediate Similarity	NPC131350
0.7658	Intermediate Similarity	NPC470777
0.7647	Intermediate Similarity	NPC259654
0.7647	Intermediate Similarity	NPC298266
0.7642	Intermediate Similarity	NPC208333
0.7642	Intermediate Similarity	NPC227879
0.7642	Intermediate Similarity	NPC87393
0.7642	Intermediate Similarity	NPC469825
0.7642	Intermediate Similarity	NPC228190
0.7642	Intermediate Similarity	NPC236753
0.7636	Intermediate Similarity	NPC122033
0.7636	Intermediate Similarity	NPC287343
0.7636	Intermediate Similarity	NPC474654
0.7636	Intermediate Similarity	NPC97908
0.7636	Intermediate Similarity	NPC470854
0.7636	Intermediate Similarity	NPC179429
0.7634	Intermediate Similarity	NPC472744
0.7634	Intermediate Similarity	NPC15091
0.7634	Intermediate Similarity	NPC269684
0.7634	Intermediate Similarity	NPC327451
0.7634	Intermediate Similarity	NPC472847
0.7629	Intermediate Similarity	NPC50443
0.7629	Intermediate Similarity	NPC470114
0.7629	Intermediate Similarity	NPC476296
0.7629	Intermediate Similarity	NPC18536
0.7624	Intermediate Similarity	NPC476294
0.7619	Intermediate Similarity	NPC186054
0.7615	Intermediate Similarity	NPC477465
0.7614	Intermediate Similarity	NPC317212
0.7609	Intermediate Similarity	NPC329490
0.7609	Intermediate Similarity	NPC58631
0.7609	Intermediate Similarity	NPC328639
0.7604	Intermediate Similarity	NPC476379
0.76	Intermediate Similarity	NPC256227
0.76	Intermediate Similarity	NPC475765
0.76	Intermediate Similarity	NPC476728
0.7596	Intermediate Similarity	NPC267637
0.7593	Intermediate Similarity	NPC473352
0.7593	Intermediate Similarity	NPC157571
0.7582	Intermediate Similarity	NPC472310
0.7582	Intermediate Similarity	NPC320144
0.7579	Intermediate Similarity	NPC474215
0.7579	Intermediate Similarity	NPC476727
0.7579	Intermediate Similarity	NPC472272
0.7579	Intermediate Similarity	NPC476726
0.7579	Intermediate Similarity	NPC475729
0.7576	Intermediate Similarity	NPC470424
0.757	Intermediate Similarity	NPC66513
0.757	Intermediate Similarity	NPC100908
0.757	Intermediate Similarity	NPC471093
0.7568	Intermediate Similarity	NPC470776
0.7553	Intermediate Similarity	NPC319909
0.7553	Intermediate Similarity	NPC65133
0.7553	Intermediate Similarity	NPC473336
0.7553	Intermediate Similarity	NPC471044
0.7553	Intermediate Similarity	NPC50438
0.7551	Intermediate Similarity	NPC475878
0.7549	Intermediate Similarity	NPC477656
0.7547	Intermediate Similarity	NPC471094
0.7547	Intermediate Similarity	NPC469826
0.7547	Intermediate Similarity	NPC469984
0.7547	Intermediate Similarity	NPC473410
0.7547	Intermediate Similarity	NPC316930
0.7547	Intermediate Similarity	NPC207693
0.7527	Intermediate Similarity	NPC317066
0.7527	Intermediate Similarity	NPC477936
0.7527	Intermediate Similarity	NPC13494
0.7527	Intermediate Similarity	NPC477935
0.7527	Intermediate Similarity	NPC328007
0.7524	Intermediate Similarity	NPC273189
0.7524	Intermediate Similarity	NPC184805
0.7523	Intermediate Similarity	NPC49451
0.7523	Intermediate Similarity	NPC97002
0.75	Intermediate Similarity	NPC266
0.75	Intermediate Similarity	NPC17336
0.75	Intermediate Similarity	NPC305808
0.75	Intermediate Similarity	NPC139347
0.75	Intermediate Similarity	NPC109510
0.75	Intermediate Similarity	NPC157476
0.75	Intermediate Similarity	NPC209298

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 NPC247877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	505
0.1-0.2	3599
0.2-0.3	3319
0.3-0.4	1054
0.4-0.5	342
0.5-0.6	196
0.6-0.7	121
0.7-0.8	14
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
0.7714	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6116	Phase 1
0.7253	Intermediate Similarity	NPD6117	Approved
0.7168	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1700	Approved
0.7143	Intermediate Similarity	NPD3703	Phase 2
0.7103	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD6118	Approved
0.7097	Intermediate Similarity	NPD6114	Approved
0.7097	Intermediate Similarity	NPD6697	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3702	Approved
0.6949	Remote Similarity	NPD8328	Phase 3
0.6923	Remote Similarity	NPD6921	Approved
0.6881	Remote Similarity	NPD5739	Approved
0.6881	Remote Similarity	NPD6402	Approved
0.6881	Remote Similarity	NPD6675	Approved
0.6881	Remote Similarity	NPD7128	Approved
0.6863	Remote Similarity	NPD8035	Phase 2
0.6863	Remote Similarity	NPD8034	Phase 2
0.6847	Remote Similarity	NPD6373	Approved
0.6847	Remote Similarity	NPD6372	Approved
0.6838	Remote Similarity	NPD6319	Approved
0.6818	Remote Similarity	NPD5701	Approved
0.6818	Remote Similarity	NPD5697	Approved
0.6814	Remote Similarity	NPD8297	Approved
0.6813	Remote Similarity	NPD6081	Approved
0.6813	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7320	Approved
0.6757	Remote Similarity	NPD6881	Approved
0.6757	Remote Similarity	NPD6899	Approved
0.6726	Remote Similarity	NPD6649	Approved
0.6726	Remote Similarity	NPD6650	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.6703	Remote Similarity	NPD4789	Approved
0.6696	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6013	Approved
0.6696	Remote Similarity	NPD6014	Approved
0.6696	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD7102	Approved
0.6637	Remote Similarity	NPD7290	Approved
0.6637	Remote Similarity	NPD6883	Approved
0.663	Remote Similarity	NPD5777	Approved
0.6629	Remote Similarity	NPD4224	Phase 2
0.6612	Remote Similarity	NPD7492	Approved
0.6609	Remote Similarity	NPD4632	Approved
0.6607	Remote Similarity	NPD6011	Approved
0.66	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3698	Phase 2
0.6581	Remote Similarity	NPD7115	Discovery
0.6579	Remote Similarity	NPD8130	Phase 1
0.6579	Remote Similarity	NPD6847	Approved
0.6579	Remote Similarity	NPD6869	Approved
0.6579	Remote Similarity	NPD6617	Approved
0.6557	Remote Similarity	NPD6616	Approved
0.6555	Remote Similarity	NPD6054	Approved
0.6555	Remote Similarity	NPD6059	Approved
0.6542	Remote Similarity	NPD7902	Approved
0.6542	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD4244	Approved
0.6522	Remote Similarity	NPD4245	Approved
0.6522	Remote Similarity	NPD6882	Approved
0.6504	Remote Similarity	NPD8293	Discontinued
0.6504	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD6015	Approved
0.6491	Remote Similarity	NPD4634	Approved
0.6484	Remote Similarity	NPD5360	Phase 3
0.6484	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5696	Approved
0.6481	Remote Similarity	NPD4225	Approved
0.6466	Remote Similarity	NPD8133	Approved
0.6446	Remote Similarity	NPD6370	Approved
0.6446	Remote Similarity	NPD5988	Approved
0.6435	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5286	Approved
0.6422	Remote Similarity	NPD5285	Approved
0.6422	Remote Similarity	NPD4700	Approved
0.6422	Remote Similarity	NPD4696	Approved
0.6415	Remote Similarity	NPD7748	Approved
0.6404	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7319	Approved
0.6392	Remote Similarity	NPD3671	Phase 1
0.6381	Remote Similarity	NPD7515	Phase 2
0.6364	Remote Similarity	NPD1779	Approved
0.6364	Remote Similarity	NPD1780	Approved
0.6356	Remote Similarity	NPD6274	Approved
0.6339	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6399	Phase 3
0.6306	Remote Similarity	NPD5225	Approved
0.6306	Remote Similarity	NPD4633	Approved
0.6306	Remote Similarity	NPD5226	Approved
0.6306	Remote Similarity	NPD5211	Phase 2
0.6306	Remote Similarity	NPD5224	Approved
0.6304	Remote Similarity	NPD229	Approved
0.6303	Remote Similarity	NPD6009	Approved
0.6296	Remote Similarity	NPD4697	Phase 3
0.629	Remote Similarity	NPD7507	Approved
0.6277	Remote Similarity	NPD4758	Discontinued
0.6262	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD6084	Phase 2
0.6239	Remote Similarity	NPD6083	Phase 2
0.6238	Remote Similarity	NPD3669	Approved
0.6238	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5983	Phase 2
0.6226	Remote Similarity	NPD6411	Approved
0.6218	Remote Similarity	NPD6940	Discontinued
0.6216	Remote Similarity	NPD5223	Approved
0.6207	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7101	Approved
0.6198	Remote Similarity	NPD7100	Approved
0.6195	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD8171	Discontinued
0.6167	Remote Similarity	NPD6317	Approved
0.6154	Remote Similarity	NPD3573	Approved
0.6147	Remote Similarity	NPD5222	Approved
0.6147	Remote Similarity	NPD5221	Approved
0.6147	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6920	Discontinued
0.614	Remote Similarity	NPD4767	Approved
0.614	Remote Similarity	NPD6008	Approved
0.614	Remote Similarity	NPD4768	Approved
0.6129	Remote Similarity	NPD7604	Phase 2
0.6116	Remote Similarity	NPD6335	Approved
0.6116	Remote Similarity	NPD6314	Approved
0.6116	Remote Similarity	NPD6313	Approved
0.6106	Remote Similarity	NPD4754	Approved
0.61	Remote Similarity	NPD6928	Phase 2
0.6098	Remote Similarity	NPD6909	Approved
0.6098	Remote Similarity	NPD6908	Approved
0.6091	Remote Similarity	NPD5173	Approved
0.6087	Remote Similarity	NPD6412	Phase 2
0.6063	Remote Similarity	NPD6033	Approved
0.6061	Remote Similarity	NPD5364	Discontinued
0.6058	Remote Similarity	NPD3618	Phase 1
0.6055	Remote Similarity	NPD5695	Phase 3
0.6055	Remote Similarity	NPD5210	Approved
0.6055	Remote Similarity	NPD4629	Approved
0.6044	Remote Similarity	NPD371	Approved
0.6038	Remote Similarity	NPD6101	Approved
0.6038	Remote Similarity	NPD5328	Approved
0.6038	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4729	Approved
0.6034	Remote Similarity	NPD5128	Approved
0.6034	Remote Similarity	NPD4730	Approved
0.6032	Remote Similarity	NPD6336	Discontinued
0.5978	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8517	Approved
0.5968	Remote Similarity	NPD8513	Phase 3
0.5968	Remote Similarity	NPD8515	Approved
0.5968	Remote Similarity	NPD8516	Approved
0.595	Remote Similarity	NPD6868	Approved
0.5948	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5247	Approved
0.5932	Remote Similarity	NPD5249	Phase 3
0.5932	Remote Similarity	NPD5251	Approved
0.5932	Remote Similarity	NPD5248	Approved
0.5932	Remote Similarity	NPD5250	Approved
0.5926	Remote Similarity	NPD6079	Approved
0.5905	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4238	Approved
0.59	Remote Similarity	NPD4802	Phase 2
0.5897	Remote Similarity	NPD6686	Approved
0.5893	Remote Similarity	NPD7638	Approved
0.5888	Remote Similarity	NPD4753	Phase 2
0.5882	Remote Similarity	NPD5217	Approved
0.5882	Remote Similarity	NPD5216	Approved
0.5882	Remote Similarity	NPD5215	Approved
0.5877	Remote Similarity	NPD8086	Approved
0.5877	Remote Similarity	NPD8083	Approved
0.5877	Remote Similarity	NPD8082	Approved
0.5877	Remote Similarity	NPD8138	Approved
0.5877	Remote Similarity	NPD8139	Approved
0.5877	Remote Similarity	NPD8084	Approved
0.5877	Remote Similarity	NPD8085	Approved
0.5872	Remote Similarity	NPD4202	Approved
0.587	Remote Similarity	NPD7909	Approved
0.5841	Remote Similarity	NPD8418	Phase 2
0.5841	Remote Similarity	NPD7639	Approved
0.5841	Remote Similarity	NPD7640	Approved
0.5826	Remote Similarity	NPD8276	Approved
0.5826	Remote Similarity	NPD8275	Approved
0.5825	Remote Similarity	NPD3667	Approved
0.5818	Remote Similarity	NPD5282	Discontinued
0.5798	Remote Similarity	NPD5169	Approved
0.5798	Remote Similarity	NPD5135	Approved
0.5798	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6672	Approved
0.5794	Remote Similarity	NPD7513	Clinical (unspecified phase)

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