NPASS Compound

Structure

CID47880 OpenBabel06191715382D 30 31 0 0 1 0 0 0 0 0999 V2000 -1.9009 -6.1105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3022 -5.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0594 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -2.5772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8422 -2.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7843 -1.5642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 1.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0050 0.5354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7199 -4.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3077 -5.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2673 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0991 -3.1435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2129 -0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1266 -3.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9456 -1.7518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9401 -1.8563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8061 -1.3563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3070 -4.1216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2074 -0.5473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 -3.3698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1151 -2.3074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1480 -2.8345 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 -1.5388 -2.6654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 4 13 2 0 0 0 0 5 14 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 12 3 1 6 0 0 0 13 21 1 0 0 0 0 14 23 2 0 0 0 0 14 28 1 0 0 0 0 15 10 1 1 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 16 24 2 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 18 13 1 6 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 6 0 0 0 20 22 1 1 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 6 1 1 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.19
Volume:	426.458
LogP:	2.482
LogD:	1.503
LogS:	-3.295
# Rotatable Bonds:	6
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.317
Synthetic Accessibility Score:	5.041
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.718
MDCK Permeability:	4.6958663006080315e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.142
20% Bioavailability (F20%):	0.145
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.704
Plasma Protein Binding (PPB):	60.496360778808594%
Volume Distribution (VD):	0.588
Pgp-substrate:	31.268962860107422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	8.145
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.617
Drug-inuced Liver Injury (DILI):	0.889
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.647
Carcinogencity:	0.689
Eye Corrosion:	0.04
Eye Irritation:	0.162
Respiratory Toxicity:	0.757

Download Data

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

Natural Product: NPC47880

Natural Product ID:	NPC47880
*Common Name:**	Neurolenin B
IUPAC Name:	[(3aS,4S,5R,6S,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] 3-methylbutanoate
Synonyms:	Neurolenin B
Standard InCHIKey:	UVRIFAYGSSDVER-MBZNIOTRSA-N
Standard InCHI:	InChI=1S/C22H30O8/c1-11(2)9-17(25)30-19-18-13(4)21(26)29-15(18)10-12(3)7-8-16(24)22(6,27)20(19)28-14(5)23/h7-8,11-12,15,18-20,27H,4,9-10H2,1-3,5-6H3/b8-7-/t12-,15+,18-,19-,20+,22+/m0/s1
SMILES:	C[C@H]1/C=CC(=O)[C@@](C)(O)[C@@H]([C@H]([C@@H]2[C@@H](C1)OC(=O)C2=C)OC(=O)CC(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173219
PubChem CID:	49799795
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1021/jo00416a020]
NPO11195	Neurolaena oaxacana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479310]
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12116880]
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	stem	n.a.	PMID[12116880]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24476550]
NPO30049	Neurolaena cobanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11911	Austroeupatorium inulifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11195	Neurolaena oaxacana	Species	Asteraceae	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	1
MIC	2

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	MIC	=	7600.0	nM	PMID[468108]
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	MIC	=	3800.0	nM	PMID[468108]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	620.0	nM	PMID[468109]

☑ 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 NPC47880 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	222
0.1-0.2	1298
0.2-0.3	4763
0.3-0.4	8261
0.4-0.5	14479
0.5-0.6	7977
0.6-0.7	4163
0.7-0.8	1280
0.8-0.85	173
0.85-0.9	75
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC149371
0.9368	High Similarity	NPC471144
0.9278	High Similarity	NPC474747
0.9184	High Similarity	NPC475871
0.9184	High Similarity	NPC475945
0.9175	High Similarity	NPC474742
0.9175	High Similarity	NPC474339
0.9175	High Similarity	NPC164598
0.91	High Similarity	NPC477513
0.9091	High Similarity	NPC474741
0.899	High Similarity	NPC475873
0.8958	High Similarity	NPC76862
0.8958	High Similarity	NPC470883
0.8958	High Similarity	NPC158416
0.8958	High Similarity	NPC39859
0.8889	High Similarity	NPC472754
0.8878	High Similarity	NPC475949
0.8878	High Similarity	NPC288876
0.8854	High Similarity	NPC471142
0.8854	High Similarity	NPC475659
0.8842	High Similarity	NPC476300
0.88	High Similarity	NPC472755
0.8788	High Similarity	NPC472753
0.8788	High Similarity	NPC476270
0.8788	High Similarity	NPC264477
0.8788	High Similarity	NPC477511
0.8788	High Similarity	NPC201718
0.8788	High Similarity	NPC15993
0.8763	High Similarity	NPC17585
0.8763	High Similarity	NPC476009
0.8763	High Similarity	NPC473859
0.875	High Similarity	NPC190294
0.8737	High Similarity	NPC184463
0.8723	High Similarity	NPC307411
0.8713	High Similarity	NPC471143
0.8713	High Similarity	NPC477510
0.8713	High Similarity	NPC472756
0.87	High Similarity	NPC471148
0.87	High Similarity	NPC320019
0.87	High Similarity	NPC324017
0.8687	High Similarity	NPC477512
0.866	High Similarity	NPC475900
0.866	High Similarity	NPC36954
0.8646	High Similarity	NPC162205
0.8646	High Similarity	NPC288240
0.8646	High Similarity	NPC475912
0.8646	High Similarity	NPC273579
0.8646	High Similarity	NPC212486
0.8646	High Similarity	NPC295204
0.8632	High Similarity	NPC179394
0.8632	High Similarity	NPC51004
0.8632	High Similarity	NPC144133
0.8632	High Similarity	NPC473619
0.8617	High Similarity	NPC202672
0.8614	High Similarity	NPC4620
0.86	High Similarity	NPC110443
0.86	High Similarity	NPC133907
0.86	High Similarity	NPC46998
0.86	High Similarity	NPC128733
0.86	High Similarity	NPC185141
0.8586	High Similarity	NPC473326
0.8571	High Similarity	NPC477921
0.8571	High Similarity	NPC230800
0.8571	High Similarity	NPC31645
0.8571	High Similarity	NPC279621
0.8558	High Similarity	NPC38154
0.8542	High Similarity	NPC473321
0.8542	High Similarity	NPC30515
0.8542	High Similarity	NPC12172
0.8542	High Similarity	NPC208886
0.8529	High Similarity	NPC100487
0.8529	High Similarity	NPC203659
0.8529	High Similarity	NPC475676
0.8529	High Similarity	NPC220964
0.8526	High Similarity	NPC151770
0.8515	High Similarity	NPC225353
0.8485	Intermediate Similarity	NPC328562
0.8485	Intermediate Similarity	NPC40812
0.8485	Intermediate Similarity	NPC323421
0.8485	Intermediate Similarity	NPC471140
0.8469	Intermediate Similarity	NPC477922
0.8469	Intermediate Similarity	NPC14961
0.8469	Intermediate Similarity	NPC471141
0.8469	Intermediate Similarity	NPC270013
0.8454	Intermediate Similarity	NPC469645
0.8454	Intermediate Similarity	NPC469692
0.8454	Intermediate Similarity	NPC179746
0.8454	Intermediate Similarity	NPC81419
0.8454	Intermediate Similarity	NPC475302
0.8447	Intermediate Similarity	NPC16313
0.8447	Intermediate Similarity	NPC9303
0.8438	Intermediate Similarity	NPC475855
0.8431	Intermediate Similarity	NPC110989
0.8384	Intermediate Similarity	NPC476315
0.8367	Intermediate Similarity	NPC473316
0.8367	Intermediate Similarity	NPC81386
0.8367	Intermediate Similarity	NPC57405
0.8367	Intermediate Similarity	NPC474247
0.8367	Intermediate Similarity	NPC303942
0.8367	Intermediate Similarity	NPC471147
0.8367	Intermediate Similarity	NPC121825
0.8367	Intermediate Similarity	NPC473330
0.8367	Intermediate Similarity	NPC474035
0.8367	Intermediate Similarity	NPC140543
0.8365	Intermediate Similarity	NPC324327
0.8365	Intermediate Similarity	NPC72813
0.8365	Intermediate Similarity	NPC474421
0.8365	Intermediate Similarity	NPC26617
0.8365	Intermediate Similarity	NPC194620
0.8365	Intermediate Similarity	NPC326994
0.8351	Intermediate Similarity	NPC20713
0.835	Intermediate Similarity	NPC472748
0.8349	Intermediate Similarity	NPC471146
0.8349	Intermediate Similarity	NPC471145
0.8333	Intermediate Similarity	NPC166919
0.8333	Intermediate Similarity	NPC474032
0.8318	Intermediate Similarity	NPC66108
0.8286	Intermediate Similarity	NPC474664
0.8286	Intermediate Similarity	NPC55972
0.8286	Intermediate Similarity	NPC327286
0.8286	Intermediate Similarity	NPC14862
0.8286	Intermediate Similarity	NPC169888
0.8286	Intermediate Similarity	NPC233379
0.8269	Intermediate Similarity	NPC472749
0.8269	Intermediate Similarity	NPC475802
0.8269	Intermediate Similarity	NPC472751
0.8265	Intermediate Similarity	NPC475838
0.8265	Intermediate Similarity	NPC228451
0.8265	Intermediate Similarity	NPC125674
0.8252	Intermediate Similarity	NPC472747
0.8252	Intermediate Similarity	NPC472750
0.8247	Intermediate Similarity	NPC474232
0.8247	Intermediate Similarity	NPC474761
0.8247	Intermediate Similarity	NPC476004
0.8247	Intermediate Similarity	NPC251385
0.8247	Intermediate Similarity	NPC475748
0.8247	Intermediate Similarity	NPC49342
0.8229	Intermediate Similarity	NPC473715
0.8218	Intermediate Similarity	NPC187761
0.8218	Intermediate Similarity	NPC308567
0.8218	Intermediate Similarity	NPC261377
0.8218	Intermediate Similarity	NPC83895
0.8218	Intermediate Similarity	NPC208233
0.8218	Intermediate Similarity	NPC474213
0.8218	Intermediate Similarity	NPC255592
0.8218	Intermediate Similarity	NPC161855
0.8208	Intermediate Similarity	NPC15218
0.82	Intermediate Similarity	NPC35498
0.82	Intermediate Similarity	NPC476275
0.8182	Intermediate Similarity	NPC476267
0.8163	Intermediate Similarity	NPC111114
0.8163	Intermediate Similarity	NPC300312
0.8163	Intermediate Similarity	NPC261607
0.8155	Intermediate Similarity	NPC183571
0.8144	Intermediate Similarity	NPC173926
0.8144	Intermediate Similarity	NPC92974
0.8144	Intermediate Similarity	NPC474951
0.8131	Intermediate Similarity	NPC5103
0.8125	Intermediate Similarity	NPC231889
0.8125	Intermediate Similarity	NPC186148
0.8119	Intermediate Similarity	NPC471462
0.8105	Intermediate Similarity	NPC319795
0.8105	Intermediate Similarity	NPC50362
0.8105	Intermediate Similarity	NPC38468
0.81	Intermediate Similarity	NPC474947
0.8095	Intermediate Similarity	NPC223450
0.8081	Intermediate Similarity	NPC165383
0.8077	Intermediate Similarity	NPC69171
0.8077	Intermediate Similarity	NPC474165
0.8061	Intermediate Similarity	NPC329857
0.8061	Intermediate Similarity	NPC65359
0.8061	Intermediate Similarity	NPC469718
0.8056	Intermediate Similarity	NPC304180
0.8056	Intermediate Similarity	NPC179798
0.8041	Intermediate Similarity	NPC58219
0.8041	Intermediate Similarity	NPC476805
0.8041	Intermediate Similarity	NPC177629
0.8041	Intermediate Similarity	NPC476803
0.8041	Intermediate Similarity	NPC475819
0.8039	Intermediate Similarity	NPC187268
0.8037	Intermediate Similarity	NPC42662
0.8037	Intermediate Similarity	NPC475922
0.8021	Intermediate Similarity	NPC469483
0.8021	Intermediate Similarity	NPC305475
0.8021	Intermediate Similarity	NPC475461
0.8021	Intermediate Similarity	NPC469910
0.8021	Intermediate Similarity	NPC50637
0.8021	Intermediate Similarity	NPC474762
0.8021	Intermediate Similarity	NPC150755
0.8021	Intermediate Similarity	NPC476015
0.802	Intermediate Similarity	NPC473291
0.8	Intermediate Similarity	NPC71589
0.8	Intermediate Similarity	NPC469632
0.7981	Intermediate Similarity	NPC105725
0.798	Intermediate Similarity	NPC70251
0.798	Intermediate Similarity	NPC475881
0.798	Intermediate Similarity	NPC470373
0.798	Intermediate Similarity	NPC470379
0.7963	Intermediate Similarity	NPC115257
0.7963	Intermediate Similarity	NPC161816

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 NPC47880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1877
0.2-0.3	3688
0.3-0.4	2180
0.4-0.5	774
0.5-0.6	300
0.6-0.7	117
0.7-0.8	12
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8365	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7983	Approved
0.77	Intermediate Similarity	NPD46	Approved
0.77	Intermediate Similarity	NPD6698	Approved
0.7647	Intermediate Similarity	NPD5282	Discontinued
0.7636	Intermediate Similarity	NPD6371	Approved
0.7525	Intermediate Similarity	NPD7838	Discovery
0.7411	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6319	Approved
0.7087	Intermediate Similarity	NPD1695	Approved
0.7037	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4225	Approved
0.7019	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.7	Intermediate Similarity	NPD8513	Phase 3
0.6991	Remote Similarity	NPD6686	Approved
0.6991	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD5779	Approved
0.6885	Remote Similarity	NPD7642	Approved
0.6863	Remote Similarity	NPD5363	Approved
0.6838	Remote Similarity	NPD4632	Approved
0.6829	Remote Similarity	NPD7492	Approved
0.6807	Remote Similarity	NPD7115	Discovery
0.68	Remote Similarity	NPD5369	Approved
0.6796	Remote Similarity	NPD5786	Approved
0.6777	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6757	Remote Similarity	NPD5344	Discontinued
0.6752	Remote Similarity	NPD8297	Approved
0.6733	Remote Similarity	NPD6435	Approved
0.6721	Remote Similarity	NPD6016	Approved
0.6721	Remote Similarity	NPD6015	Approved
0.672	Remote Similarity	NPD7078	Approved
0.672	Remote Similarity	NPD8074	Phase 3
0.6697	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6641	Remote Similarity	NPD7260	Phase 2
0.6613	Remote Similarity	NPD7830	Approved
0.6613	Remote Similarity	NPD7829	Approved
0.6613	Remote Similarity	NPD8328	Phase 3
0.6612	Remote Similarity	NPD7641	Discontinued
0.661	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD5697	Approved
0.6604	Remote Similarity	NPD6101	Approved
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4634	Approved
0.6569	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4270	Approved
0.6569	Remote Similarity	NPD4269	Approved
0.6552	Remote Similarity	NPD6881	Approved
0.6552	Remote Similarity	NPD6899	Approved
0.6538	Remote Similarity	NPD1694	Approved
0.6535	Remote Similarity	NPD5368	Approved
0.6532	Remote Similarity	NPD8080	Discontinued
0.6529	Remote Similarity	NPD6009	Approved
0.6518	Remote Similarity	NPD6648	Approved
0.6508	Remote Similarity	NPD8451	Approved
0.6505	Remote Similarity	NPD7154	Phase 3
0.6504	Remote Similarity	NPD6059	Approved
0.6496	Remote Similarity	NPD6373	Approved
0.6496	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD6013	Approved
0.6496	Remote Similarity	NPD6014	Approved
0.6496	Remote Similarity	NPD6372	Approved
0.6484	Remote Similarity	NPD7319	Approved
0.6481	Remote Similarity	NPD6411	Approved
0.6476	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD6882	Approved
0.6457	Remote Similarity	NPD8293	Discontinued
0.6457	Remote Similarity	NPD8448	Approved
0.6452	Remote Similarity	NPD8444	Approved
0.6452	Remote Similarity	NPD6921	Approved
0.6452	Remote Similarity	NPD5983	Phase 2
0.6441	Remote Similarity	NPD7290	Approved
0.6441	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6883	Approved
0.6441	Remote Similarity	NPD7102	Approved
0.6415	Remote Similarity	NPD4251	Approved
0.6415	Remote Similarity	NPD4250	Approved
0.641	Remote Similarity	NPD6011	Approved
0.6408	Remote Similarity	NPD5209	Approved
0.6387	Remote Similarity	NPD6617	Approved
0.6387	Remote Similarity	NPD8130	Phase 1
0.6387	Remote Similarity	NPD6869	Approved
0.6387	Remote Similarity	NPD2204	Approved
0.6387	Remote Similarity	NPD6847	Approved
0.6379	Remote Similarity	NPD7128	Approved
0.6379	Remote Similarity	NPD5739	Approved
0.6379	Remote Similarity	NPD6402	Approved
0.6379	Remote Similarity	NPD6008	Approved
0.6379	Remote Similarity	NPD6675	Approved
0.6378	Remote Similarity	NPD7507	Approved
0.6373	Remote Similarity	NPD4252	Approved
0.6356	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7604	Phase 2
0.6346	Remote Similarity	NPD6110	Phase 1
0.6336	Remote Similarity	NPD6845	Suspended
0.6325	Remote Similarity	NPD5701	Approved
0.632	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8390	Approved
0.6308	Remote Similarity	NPD8391	Approved
0.6308	Remote Similarity	NPD8392	Approved
0.6306	Remote Similarity	NPD5695	Phase 3
0.6299	Remote Similarity	NPD8340	Approved
0.6299	Remote Similarity	NPD8299	Approved
0.6299	Remote Similarity	NPD8342	Approved
0.6299	Remote Similarity	NPD8341	Approved
0.6283	Remote Similarity	NPD5696	Approved
0.6271	Remote Similarity	NPD7320	Approved
0.6261	Remote Similarity	NPD5211	Phase 2
0.626	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7500	Approved
0.625	Remote Similarity	NPD6336	Discontinued
0.625	Remote Similarity	NPD8273	Phase 1
0.625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.6214	Remote Similarity	NPD4822	Approved
0.6214	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4821	Approved
0.6214	Remote Similarity	NPD4819	Approved
0.6214	Remote Similarity	NPD4820	Approved
0.6195	Remote Similarity	NPD6083	Phase 2
0.6195	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD5362	Discontinued
0.6186	Remote Similarity	NPD6412	Phase 2
0.6186	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5141	Approved
0.614	Remote Similarity	NPD7638	Approved
0.6129	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6399	Phase 3
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6119	Remote Similarity	NPD8415	Approved
0.6087	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD7639	Approved
0.6078	Remote Similarity	NPD4756	Discovery
0.6075	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6063	Remote Similarity	NPD8267	Approved
0.6063	Remote Similarity	NPD8266	Approved
0.6063	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8269	Approved
0.6063	Remote Similarity	NPD8268	Approved
0.6061	Remote Similarity	NPD5956	Approved
0.6053	Remote Similarity	NPD4755	Approved
0.6048	Remote Similarity	NPD6274	Approved
0.6042	Remote Similarity	NPD7331	Phase 2
0.6036	Remote Similarity	NPD5693	Phase 1
0.6036	Remote Similarity	NPD7637	Suspended
0.6034	Remote Similarity	NPD5223	Approved
0.6032	Remote Similarity	NPD7100	Approved
0.6032	Remote Similarity	NPD7101	Approved
0.6031	Remote Similarity	NPD6033	Approved
0.6019	Remote Similarity	NPD4271	Approved
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4268	Approved
0.6018	Remote Similarity	NPD4629	Approved
0.6018	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD5370	Suspended
0.5984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5222	Approved
0.5965	Remote Similarity	NPD5221	Approved
0.5965	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD6313	Approved
0.5952	Remote Similarity	NPD6335	Approved
0.5952	Remote Similarity	NPD6314	Approved
0.5948	Remote Similarity	NPD4700	Approved
0.5938	Remote Similarity	NPD7503	Approved
0.5938	Remote Similarity	NPD7341	Phase 2
0.5938	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7902	Approved
0.5913	Remote Similarity	NPD5173	Approved
0.5909	Remote Similarity	NPD5737	Approved
0.5909	Remote Similarity	NPD6672	Approved
0.5906	Remote Similarity	NPD4522	Approved
0.5905	Remote Similarity	NPD4695	Discontinued
0.5902	Remote Similarity	NPD5251	Approved
0.5902	Remote Similarity	NPD5247	Approved
0.5902	Remote Similarity	NPD5248	Approved
0.5902	Remote Similarity	NPD5249	Phase 3

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