NPASS Compound

Structure

CID101138 OpenBabel06191715442D 26 30 0 0 1 0 0 0 0 0999 V2000 3.0120 -2.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9266 -2.1456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4635 1.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6021 -2.7750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8133 -3.2864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -2.8169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3911 -2.3195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8131 -2.3195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6264 -1.8779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0682 -0.7989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8132 -0.4695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0959 -2.0037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6264 -2.8169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8779 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6021 -0.9530 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7522 -1.4084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7916 -0.0618 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8132 -0.4695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3911 -1.4085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8131 -1.4085 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8132 -1.4084 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2102 -0.6151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6022 -0.0139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1820 0.6152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6976 0.0334 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 3 24 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 6 14 1 0 0 0 0 7 19 1 0 0 0 0 9 13 1 0 0 0 0 10 19 1 0 0 0 0 10 25 1 0 0 0 0 11 20 1 0 0 0 0 11 26 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 5 1 6 0 0 0 14 20 1 1 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 1 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 2 1 6 0 0 0 20 8 1 1 0 0 0 21 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	367.668
LogP:	2.919
LogD:	3.103
LogS:	-4.56
# Rotatable Bonds:	1
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	6.516
Fsp3:	0.905
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.162
MDCK Permeability:	3.102089976891875e-05
Pgp-inhibitor:	0.17
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.893
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.495
Plasma Protein Binding (PPB):	88.31163787841797%
Volume Distribution (VD):	1.649
Pgp-substrate:	4.55397891998291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	8.937
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.629
AMES Toxicity:	0.322
Rat Oral Acute Toxicity:	0.737
Maximum Recommended Daily Dose:	0.607
Skin Sensitization:	0.076
Carcinogencity:	0.382
Eye Corrosion:	0.075
Eye Irritation:	0.453
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC101138

Natural Product ID:	NPC101138
*Common Name:**	Ludongnin G
IUPAC Name:	n.a.
Synonyms:	Ludongnin G
Standard InCHIKey:	YPVJSAYFTDREBJ-KAQOAFHOSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-12-13-5-6-14-20(11-26-18(23)21(14,9-13)16(12)22)8-4-7-19(2)10-25-17(24-3)15(19)20/h12-15,17H,4-11H2,1-3H3/t12-,13+,14-,15+,17+,19-,20+,21-/m0/s1
SMILES:	C[C@H]1[C@@H]2CC[C@H]3[C@@]4(CCC[C@@]5(C)CO[C@H]([C@@H]45)OC)COC(=O)[C@]3(C2)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511568
PubChem CID:	11417148
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
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575445]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20521771]
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]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[515776]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[515777]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[515777]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[515777]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	10000.0	nM	PMID[515777]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	10000.0	nM	PMID[515777]

☑ 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 NPC101138 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	434
0.1-0.2	4356
0.2-0.3	12317
0.3-0.4	11256
0.4-0.5	6206
0.5-0.6	5854
0.6-0.7	1960
0.7-0.8	279
0.8-0.85	16
0.85-0.9	14
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC51135
1.0	High Similarity	NPC25802
1.0	High Similarity	NPC82492
0.9241	High Similarity	NPC1882
0.875	High Similarity	NPC41649
0.8556	High Similarity	NPC193785
0.8295	Intermediate Similarity	NPC200580
0.8118	Intermediate Similarity	NPC24556
0.7938	Intermediate Similarity	NPC88469
0.7938	Intermediate Similarity	NPC244247
0.7901	Intermediate Similarity	NPC248567
0.7857	Intermediate Similarity	NPC164600
0.7857	Intermediate Similarity	NPC103172
0.7791	Intermediate Similarity	NPC472230
0.7791	Intermediate Similarity	NPC472229
0.7778	Intermediate Similarity	NPC221993
0.7765	Intermediate Similarity	NPC474754
0.7755	Intermediate Similarity	NPC101842
0.7738	Intermediate Similarity	NPC477918
0.7738	Intermediate Similarity	NPC169389
0.7701	Intermediate Similarity	NPC13494
0.7674	Intermediate Similarity	NPC60568
0.7634	Intermediate Similarity	NPC161035
0.7634	Intermediate Similarity	NPC472238
0.7634	Intermediate Similarity	NPC472237
0.76	Intermediate Similarity	NPC96333
0.76	Intermediate Similarity	NPC61071
0.76	Intermediate Similarity	NPC88833
0.7582	Intermediate Similarity	NPC33398
0.7561	Intermediate Similarity	NPC197701
0.7556	Intermediate Similarity	NPC244174
0.7549	Intermediate Similarity	NPC98069
0.7549	Intermediate Similarity	NPC49730
0.7529	Intermediate Similarity	NPC471151
0.7528	Intermediate Similarity	NPC473336
0.7528	Intermediate Similarity	NPC471044
0.7527	Intermediate Similarity	NPC475878
0.75	Intermediate Similarity	NPC472273
0.75	Intermediate Similarity	NPC477934
0.7474	Intermediate Similarity	NPC305808
0.7474	Intermediate Similarity	NPC215570
0.7473	Intermediate Similarity	NPC265580
0.7471	Intermediate Similarity	NPC125366
0.747	Intermediate Similarity	NPC474755
0.7449	Intermediate Similarity	NPC178853
0.7412	Intermediate Similarity	NPC477933
0.7412	Intermediate Similarity	NPC477932
0.7412	Intermediate Similarity	NPC471046
0.7391	Intermediate Similarity	NPC56413
0.7353	Intermediate Similarity	NPC224414
0.7349	Intermediate Similarity	NPC469940
0.7347	Intermediate Similarity	NPC267921
0.734	Intermediate Similarity	NPC474631
0.7327	Intermediate Similarity	NPC285927
0.732	Intermediate Similarity	NPC266417
0.7312	Intermediate Similarity	NPC472233
0.7312	Intermediate Similarity	NPC472234
0.73	Intermediate Similarity	NPC107385
0.7294	Intermediate Similarity	NPC472311
0.7294	Intermediate Similarity	NPC132064
0.7283	Intermediate Similarity	NPC252714
0.7282	Intermediate Similarity	NPC471250
0.7282	Intermediate Similarity	NPC469825
0.7273	Intermediate Similarity	NPC478181
0.7273	Intermediate Similarity	NPC134227
0.7263	Intermediate Similarity	NPC476189
0.7253	Intermediate Similarity	NPC473350
0.7228	Intermediate Similarity	NPC470167
0.7228	Intermediate Similarity	NPC469827
0.7222	Intermediate Similarity	NPC217559
0.7222	Intermediate Similarity	NPC292458
0.7222	Intermediate Similarity	NPC15821
0.7222	Intermediate Similarity	NPC268578
0.7216	Intermediate Similarity	NPC475785
0.7216	Intermediate Similarity	NPC476728
0.7216	Intermediate Similarity	NPC475765
0.7212	Intermediate Similarity	NPC98633
0.7212	Intermediate Similarity	NPC106760
0.72	Intermediate Similarity	NPC471254
0.72	Intermediate Similarity	NPC470172
0.7191	Intermediate Similarity	NPC45256
0.7191	Intermediate Similarity	NPC260977
0.7191	Intermediate Similarity	NPC285480
0.7191	Intermediate Similarity	NPC30443
0.7184	Intermediate Similarity	NPC469826
0.7184	Intermediate Similarity	NPC469845
0.7184	Intermediate Similarity	NPC232133
0.7176	Intermediate Similarity	NPC477867
0.7176	Intermediate Similarity	NPC55508
0.7176	Intermediate Similarity	NPC477930
0.7174	Intermediate Similarity	NPC477441
0.7157	Intermediate Similarity	NPC215408
0.7143	Intermediate Similarity	NPC65133
0.7143	Intermediate Similarity	NPC470243
0.7143	Intermediate Similarity	NPC473062
0.7143	Intermediate Similarity	NPC477434
0.7143	Intermediate Similarity	NPC272242
0.7143	Intermediate Similarity	NPC471251
0.7143	Intermediate Similarity	NPC319909
0.7129	Intermediate Similarity	NPC473406
0.7129	Intermediate Similarity	NPC471253
0.7128	Intermediate Similarity	NPC67653
0.7128	Intermediate Similarity	NPC61688
0.7128	Intermediate Similarity	NPC471459
0.7126	Intermediate Similarity	NPC70996
0.7115	Intermediate Similarity	NPC469983
0.7113	Intermediate Similarity	NPC62407
0.7113	Intermediate Similarity	NPC287354
0.7111	Intermediate Similarity	NPC102156
0.7111	Intermediate Similarity	NPC148740
0.7111	Intermediate Similarity	NPC242771
0.7111	Intermediate Similarity	NPC477935
0.7111	Intermediate Similarity	NPC164289
0.7111	Intermediate Similarity	NPC311642
0.7111	Intermediate Similarity	NPC477936
0.7111	Intermediate Similarity	NPC61107
0.7111	Intermediate Similarity	NPC100366
0.7111	Intermediate Similarity	NPC289486
0.7108	Intermediate Similarity	NPC295788
0.7103	Intermediate Similarity	NPC79193
0.7089	Intermediate Similarity	NPC306750
0.7083	Intermediate Similarity	NPC228700
0.7083	Intermediate Similarity	NPC472231
0.7083	Intermediate Similarity	NPC472232
0.7083	Intermediate Similarity	NPC474379
0.7079	Intermediate Similarity	NPC170038
0.7079	Intermediate Similarity	NPC472853
0.7079	Intermediate Similarity	NPC471216
0.7079	Intermediate Similarity	NPC475456
0.7079	Intermediate Similarity	NPC471217
0.7071	Intermediate Similarity	NPC26270
0.7065	Intermediate Similarity	NPC477205
0.7059	Intermediate Similarity	NPC109510
0.7053	Intermediate Similarity	NPC77756
0.7048	Intermediate Similarity	NPC124053
0.7048	Intermediate Similarity	NPC130302
0.7048	Intermediate Similarity	NPC255655
0.7045	Intermediate Similarity	NPC185465
0.7041	Intermediate Similarity	NPC116683
0.7033	Intermediate Similarity	NPC472847
0.703	Intermediate Similarity	NPC213528
0.703	Intermediate Similarity	NPC94919
0.703	Intermediate Similarity	NPC244969
0.7024	Intermediate Similarity	NPC477929
0.7021	Intermediate Similarity	NPC90676
0.7019	Intermediate Similarity	NPC92890
0.7019	Intermediate Similarity	NPC202898
0.7019	Intermediate Similarity	NPC475319
0.701	Intermediate Similarity	NPC206878
0.701	Intermediate Similarity	NPC470424
0.7009	Intermediate Similarity	NPC285086
0.7009	Intermediate Similarity	NPC102619
0.7	Intermediate Similarity	NPC58631
0.7	Intermediate Similarity	NPC271572
0.7	Intermediate Similarity	NPC71541
0.7	Intermediate Similarity	NPC20028
0.7	Intermediate Similarity	NPC474870
0.7	Intermediate Similarity	NPC41843
0.7	Intermediate Similarity	NPC80417
0.6989	Remote Similarity	NPC92139
0.6989	Remote Similarity	NPC474008
0.6981	Remote Similarity	NPC329953
0.6981	Remote Similarity	NPC469824
0.6979	Remote Similarity	NPC52756
0.6979	Remote Similarity	NPC470230
0.6972	Remote Similarity	NPC179429
0.697	Remote Similarity	NPC74466
0.697	Remote Similarity	NPC253586
0.697	Remote Similarity	NPC187159
0.697	Remote Similarity	NPC469810
0.697	Remote Similarity	NPC471241
0.697	Remote Similarity	NPC96839
0.6966	Remote Similarity	NPC31302
0.6966	Remote Similarity	NPC80891
0.6966	Remote Similarity	NPC320144
0.6966	Remote Similarity	NPC245029
0.6966	Remote Similarity	NPC477287
0.6966	Remote Similarity	NPC118987
0.6966	Remote Similarity	NPC201276
0.6961	Remote Similarity	NPC139347
0.6961	Remote Similarity	NPC34562
0.6957	Remote Similarity	NPC237938
0.6957	Remote Similarity	NPC9060
0.6957	Remote Similarity	NPC219535
0.6957	Remote Similarity	NPC181871
0.6952	Remote Similarity	NPC273002
0.6952	Remote Similarity	NPC92297
0.6952	Remote Similarity	NPC233433
0.6952	Remote Similarity	NPC227879
0.6952	Remote Similarity	NPC208333
0.6952	Remote Similarity	NPC473817
0.6952	Remote Similarity	NPC220836
0.6952	Remote Similarity	NPC94086
0.6951	Remote Similarity	NPC477931
0.6951	Remote Similarity	NPC268736
0.6947	Remote Similarity	NPC477443
0.6947	Remote Similarity	NPC471043
0.6947	Remote Similarity	NPC477440
0.6941	Remote Similarity	NPC473267
0.6941	Remote Similarity	NPC478227

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 NPC101138 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	449
0.1-0.2	4026
0.2-0.3	3240
0.3-0.4	850
0.4-0.5	264
0.5-0.6	245
0.6-0.7	64
0.7-0.8	12
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	NPD3702	Approved
0.7349	Intermediate Similarity	NPD5777	Approved
0.7228	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1779	Approved
0.7191	Intermediate Similarity	NPD1780	Approved
0.6951	Remote Similarity	NPD4224	Phase 2
0.6941	Remote Similarity	NPD6081	Approved
0.6932	Remote Similarity	NPD6116	Phase 1
0.6854	Remote Similarity	NPD6115	Approved
0.6854	Remote Similarity	NPD6697	Approved
0.6854	Remote Similarity	NPD6118	Approved
0.6854	Remote Similarity	NPD6114	Approved
0.6829	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6117	Approved
0.6782	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6928	Phase 2
0.6628	Remote Similarity	NPD4789	Approved
0.6552	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3703	Phase 2
0.6512	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3698	Phase 2
0.6509	Remote Similarity	NPD6008	Approved
0.6495	Remote Similarity	NPD5737	Approved
0.6495	Remote Similarity	NPD6672	Approved
0.6489	Remote Similarity	NPD3669	Approved
0.6489	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4802	Phase 2
0.6484	Remote Similarity	NPD4238	Approved
0.6449	Remote Similarity	NPD6412	Phase 2
0.6441	Remote Similarity	NPD8293	Discontinued
0.6437	Remote Similarity	NPD4245	Approved
0.6437	Remote Similarity	NPD4244	Approved
0.64	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD8171	Discontinued
0.6395	Remote Similarity	NPD5360	Phase 3
0.6395	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7736	Approved
0.6379	Remote Similarity	NPD6370	Approved
0.6327	Remote Similarity	NPD6903	Approved
0.63	Remote Similarity	NPD8034	Phase 2
0.63	Remote Similarity	NPD8035	Phase 2
0.6289	Remote Similarity	NPD6409	Approved
0.6289	Remote Similarity	NPD7334	Approved
0.6289	Remote Similarity	NPD5330	Approved
0.6289	Remote Similarity	NPD7146	Approved
0.6289	Remote Similarity	NPD6684	Approved
0.6289	Remote Similarity	NPD7521	Approved
0.6286	Remote Similarity	NPD1700	Approved
0.6283	Remote Similarity	NPD6940	Discontinued
0.6275	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7492	Approved
0.6262	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2687	Approved
0.625	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD2686	Approved
0.625	Remote Similarity	NPD2254	Approved
0.6218	Remote Similarity	NPD6616	Approved
0.6207	Remote Similarity	NPD6054	Approved
0.6207	Remote Similarity	NPD6059	Approved
0.6207	Remote Similarity	NPD229	Approved
0.6198	Remote Similarity	NPD7319	Approved
0.6182	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4758	Discontinued
0.6167	Remote Similarity	NPD7078	Approved
0.6162	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6016	Approved
0.6154	Remote Similarity	NPD6015	Approved
0.6122	Remote Similarity	NPD6098	Approved
0.6102	Remote Similarity	NPD5988	Approved
0.61	Remote Similarity	NPD6673	Approved
0.61	Remote Similarity	NPD6904	Approved
0.61	Remote Similarity	NPD6080	Approved
0.6091	Remote Similarity	NPD6686	Approved
0.6087	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7507	Approved
0.604	Remote Similarity	NPD5207	Approved
0.602	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6001	Approved
0.6018	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.598	Remote Similarity	NPD5693	Phase 1
0.5962	Remote Similarity	NPD5695	Phase 3
0.5962	Remote Similarity	NPD7991	Discontinued
0.5957	Remote Similarity	NPD3671	Phase 1
0.5957	Remote Similarity	NPD5364	Discontinued
0.5948	Remote Similarity	NPD6009	Approved
0.5946	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7320	Approved
0.5943	Remote Similarity	NPD5696	Approved
0.5917	Remote Similarity	NPD8328	Phase 3
0.5909	Remote Similarity	NPD5739	Approved
0.5909	Remote Similarity	NPD7128	Approved
0.5909	Remote Similarity	NPD6402	Approved
0.5909	Remote Similarity	NPD6675	Approved
0.5882	Remote Similarity	NPD5692	Phase 3
0.587	Remote Similarity	NPD1811	Approved
0.587	Remote Similarity	NPD1810	Approved
0.5862	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5697	Approved
0.5856	Remote Similarity	NPD5701	Approved
0.5854	Remote Similarity	NPD6033	Approved
0.5854	Remote Similarity	NPD8336	Approved
0.5854	Remote Similarity	NPD8337	Approved
0.5825	Remote Similarity	NPD6050	Approved
0.5825	Remote Similarity	NPD5694	Approved
0.5816	Remote Similarity	NPD4788	Approved
0.5806	Remote Similarity	NPD2257	Approved
0.5804	Remote Similarity	NPD6011	Approved
0.5804	Remote Similarity	NPD6881	Approved
0.5804	Remote Similarity	NPD6899	Approved
0.5798	Remote Similarity	NPD6319	Approved
0.5785	Remote Similarity	NPD6067	Discontinued
0.5758	Remote Similarity	NPD3668	Phase 3
0.5758	Remote Similarity	NPD4786	Approved
0.5752	Remote Similarity	NPD6372	Approved
0.5752	Remote Similarity	NPD6012	Approved
0.5752	Remote Similarity	NPD6373	Approved
0.5752	Remote Similarity	NPD6013	Approved
0.5752	Remote Similarity	NPD6014	Approved
0.5743	Remote Similarity	NPD3573	Approved
0.5727	Remote Similarity	NPD6052	Approved
0.5714	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7900	Approved
0.5714	Remote Similarity	NPD3667	Approved
0.5702	Remote Similarity	NPD6883	Approved
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD7102	Approved
0.569	Remote Similarity	NPD4632	Approved
0.5673	Remote Similarity	NPD5281	Approved
0.5673	Remote Similarity	NPD5284	Approved
0.566	Remote Similarity	NPD5654	Approved
0.5656	Remote Similarity	NPD7122	Discontinued
0.5652	Remote Similarity	NPD6869	Approved
0.5652	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8130	Phase 1
0.5652	Remote Similarity	NPD6847	Approved
0.5652	Remote Similarity	NPD6617	Approved
0.5652	Remote Similarity	NPD6649	Approved
0.5652	Remote Similarity	NPD6650	Approved
0.5648	Remote Similarity	NPD7638	Approved
0.5644	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD8083	Approved
0.5636	Remote Similarity	NPD8084	Approved
0.5636	Remote Similarity	NPD8138	Approved
0.5636	Remote Similarity	NPD8082	Approved
0.5636	Remote Similarity	NPD8300	Approved
0.5636	Remote Similarity	NPD8301	Approved
0.5636	Remote Similarity	NPD8086	Approved
0.5636	Remote Similarity	NPD8085	Approved
0.5636	Remote Similarity	NPD8139	Approved
0.5635	Remote Similarity	NPD5956	Approved
0.5631	Remote Similarity	NPD5328	Approved
0.5631	Remote Similarity	NPD4753	Phase 2
0.563	Remote Similarity	NPD7327	Approved
0.563	Remote Similarity	NPD7328	Approved
0.5625	Remote Similarity	NPD3617	Approved
0.5604	Remote Similarity	NPD3726	Approved
0.5604	Remote Similarity	NPD3725	Approved
0.5603	Remote Similarity	NPD8297	Approved
0.56	Remote Similarity	NPD3666	Approved
0.56	Remote Similarity	NPD3133	Approved
0.56	Remote Similarity	NPD3665	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data