NPASS Compound

Structure

NPC218107 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 -6.4416 3.5846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1379 2.8824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2012 -2.7944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1762 -2.7944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4133 2.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2922 1.8657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1816 6.0946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6160 -0.3013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1891 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7897 3.2335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2679 1.6274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5143 3.8859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3406 1.9287 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9924 2.2798 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5331 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3116 4.8396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6160 1.2763 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9197 1.9785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3775 -1.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0361 5.4920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 0.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3843 5.1409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 22 2 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 26 1 0 0 0 0 20 2 1 1 0 0 0 20 28 1 0 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 23 31 1 1 0 0 0 24 27 1 0 0 0 0 24 30 1 6 0 0 0 25 27 1 0 0 0 0 25 33 1 1 0 0 0 26 34 2 0 0 0 0 26 36 1 0 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.37
Volume:	546.548
LogP:	4.75
LogD:	3.802
LogS:	-4.34
# Rotatable Bonds:	7
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	5.166
Fsp3:	0.871
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.837
MDCK Permeability:	1.8411048586131074e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.957
Plasma Protein Binding (PPB):	58.48478698730469%
Volume Distribution (VD):	1.285
Pgp-substrate:	27.176963806152344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.6
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.891

ADMET: Excretion

Clearance (CL):	9.029
Half-life (T1/2):	0.054

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.152
Carcinogencity:	0.816
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC218107

Natural Product ID:	NPC218107
*Common Name:**	Garcihombronane B
IUPAC Name:	methyl (E,4R,6R)-6-[(3R,5S,8S,9R,10S,13S,17S)-3,9-dihydroxy-4,4,10,13,17-pentamethyl-1,2,3,5,6,7,8,11,12,16-decahydrocyclopenta[a]phenanthren-17-yl]-4-hydroxy-2-methylhept-2-enoate
Synonyms:
Standard InCHIKey:	CIVHEWNEBOOQEN-DIBHTQSVSA-N
Standard InCHI:	InChI=1S/C31H50O5/c1-19(26(34)36-8)17-21(32)18-20(2)28(5)13-11-22-23-9-10-24-27(3,4)25(33)12-14-30(24,7)31(23,35)16-15-29(22,28)6/h11,17,20-21,23-25,32-33,35H,9-10,12-16,18H2,1-8H3/b19-17+/t20-,21+,23+,24+,25-,28+,29-,30+,31-/m1/s1
SMILES:	C/C(=C[C@@H](C[C@@H](C)[C@]1(C)CC=C2[C@@H]3CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)[C@]3(CC[C@@]12C)O)O)O)/C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512141
PubChem CID:	44559190
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[476385]

☑ 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 NPC218107 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	194
0.1-0.2	1229
0.2-0.3	3974
0.3-0.4	7926
0.4-0.5	13918
0.5-0.6	6770
0.6-0.7	5848
0.7-0.8	2568
0.8-0.85	245
0.85-0.9	24
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.914	High Similarity	NPC119562
0.914	High Similarity	NPC279410
0.8947	High Similarity	NPC190713
0.8936	High Similarity	NPC476186
0.8866	High Similarity	NPC251680
0.8854	High Similarity	NPC99726
0.883	High Similarity	NPC476304
0.8776	High Similarity	NPC25177
0.8776	High Similarity	NPC222875
0.8776	High Similarity	NPC295110
0.8776	High Similarity	NPC247701
0.8776	High Similarity	NPC268829
0.8737	High Similarity	NPC57117
0.8723	High Similarity	NPC74296
0.8723	High Similarity	NPC110923
0.871	High Similarity	NPC146554
0.871	High Similarity	NPC472240
0.871	High Similarity	NPC262858
0.8673	High Similarity	NPC470074
0.8654	High Similarity	NPC470063
0.8646	High Similarity	NPC276110
0.8632	High Similarity	NPC38232
0.8632	High Similarity	NPC472871
0.8617	High Similarity	NPC78973
0.8614	High Similarity	NPC220217
0.8614	High Similarity	NPC119855
0.86	High Similarity	NPC97487
0.86	High Similarity	NPC189588
0.86	High Similarity	NPC10232
0.86	High Similarity	NPC160583
0.86	High Similarity	NPC196471
0.86	High Similarity	NPC187302
0.86	High Similarity	NPC112009
0.86	High Similarity	NPC297617
0.8571	High Similarity	NPC325229
0.8571	High Similarity	NPC92275
0.8571	High Similarity	NPC275086
0.8557	High Similarity	NPC114743
0.8557	High Similarity	NPC195366
0.8542	High Similarity	NPC105490
0.8542	High Similarity	NPC201725
0.8526	High Similarity	NPC234335
0.8526	High Similarity	NPC329842
0.8511	High Similarity	NPC314727
0.85	High Similarity	NPC475038
0.85	High Similarity	NPC109195
0.8485	Intermediate Similarity	NPC38855
0.8485	Intermediate Similarity	NPC201406
0.8485	Intermediate Similarity	NPC471041
0.8469	Intermediate Similarity	NPC253826
0.8469	Intermediate Similarity	NPC141401
0.8469	Intermediate Similarity	NPC51499
0.8447	Intermediate Similarity	NPC137462
0.8447	Intermediate Similarity	NPC304276
0.8438	Intermediate Similarity	NPC7349
0.8438	Intermediate Similarity	NPC214697
0.8431	Intermediate Similarity	NPC186668
0.8421	Intermediate Similarity	NPC295668
0.8416	Intermediate Similarity	NPC45897
0.8416	Intermediate Similarity	NPC171014
0.8416	Intermediate Similarity	NPC180204
0.8416	Intermediate Similarity	NPC472821
0.84	Intermediate Similarity	NPC471412
0.8381	Intermediate Similarity	NPC470076
0.8367	Intermediate Similarity	NPC234993
0.8367	Intermediate Similarity	NPC54248
0.8367	Intermediate Similarity	NPC276103
0.8367	Intermediate Similarity	NPC134072
0.8352	Intermediate Similarity	NPC2524
0.8351	Intermediate Similarity	NPC474922
0.8333	Intermediate Similarity	NPC472868
0.8333	Intermediate Similarity	NPC72845
0.8333	Intermediate Similarity	NPC473543
0.8333	Intermediate Similarity	NPC177641
0.8333	Intermediate Similarity	NPC212948
0.8317	Intermediate Similarity	NPC476081
0.8316	Intermediate Similarity	NPC474396
0.8316	Intermediate Similarity	NPC50488
0.8302	Intermediate Similarity	NPC44537
0.83	Intermediate Similarity	NPC324841
0.83	Intermediate Similarity	NPC471413
0.8298	Intermediate Similarity	NPC166857
0.8286	Intermediate Similarity	NPC103491
0.8286	Intermediate Similarity	NPC12795
0.8283	Intermediate Similarity	NPC231751
0.8283	Intermediate Similarity	NPC108078
0.8283	Intermediate Similarity	NPC320306
0.828	Intermediate Similarity	NPC474013
0.8269	Intermediate Similarity	NPC88701
0.8269	Intermediate Similarity	NPC275539
0.8269	Intermediate Similarity	NPC189075
0.8269	Intermediate Similarity	NPC275060
0.8265	Intermediate Similarity	NPC279974
0.8261	Intermediate Similarity	NPC476927
0.8252	Intermediate Similarity	NPC295843
0.8252	Intermediate Similarity	NPC88349
0.8252	Intermediate Similarity	NPC472818
0.8247	Intermediate Similarity	NPC205034
0.8247	Intermediate Similarity	NPC53555
0.8247	Intermediate Similarity	NPC162615
0.8247	Intermediate Similarity	NPC152778
0.8242	Intermediate Similarity	NPC159148
0.8241	Intermediate Similarity	NPC470075
0.8235	Intermediate Similarity	NPC120321
0.8235	Intermediate Similarity	NPC476237
0.8235	Intermediate Similarity	NPC85742
0.8235	Intermediate Similarity	NPC473523
0.8235	Intermediate Similarity	NPC478057
0.8235	Intermediate Similarity	NPC36688
0.8235	Intermediate Similarity	NPC95899
0.8229	Intermediate Similarity	NPC182136
0.8229	Intermediate Similarity	NPC221111
0.8229	Intermediate Similarity	NPC302280
0.8229	Intermediate Similarity	NPC280149
0.8229	Intermediate Similarity	NPC310479
0.8218	Intermediate Similarity	NPC11974
0.8218	Intermediate Similarity	NPC475617
0.8211	Intermediate Similarity	NPC472870
0.8208	Intermediate Similarity	NPC255401
0.8208	Intermediate Similarity	NPC284162
0.8208	Intermediate Similarity	NPC183603
0.82	Intermediate Similarity	NPC278673
0.82	Intermediate Similarity	NPC57079
0.82	Intermediate Similarity	NPC108368
0.8191	Intermediate Similarity	NPC175145
0.8191	Intermediate Similarity	NPC6391
0.8191	Intermediate Similarity	NPC261266
0.8191	Intermediate Similarity	NPC474970
0.8191	Intermediate Similarity	NPC131813
0.8191	Intermediate Similarity	NPC475069
0.819	Intermediate Similarity	NPC475030
0.819	Intermediate Similarity	NPC75389
0.8182	Intermediate Similarity	NPC16967
0.8182	Intermediate Similarity	NPC473153
0.8182	Intermediate Similarity	NPC235053
0.8173	Intermediate Similarity	NPC67321
0.8173	Intermediate Similarity	NPC79298
0.8173	Intermediate Similarity	NPC472820
0.8173	Intermediate Similarity	NPC471205
0.8173	Intermediate Similarity	NPC43063
0.8173	Intermediate Similarity	NPC110496
0.8173	Intermediate Similarity	NPC187435
0.8163	Intermediate Similarity	NPC191521
0.8155	Intermediate Similarity	NPC472819
0.8144	Intermediate Similarity	NPC473675
0.8144	Intermediate Similarity	NPC472811
0.8144	Intermediate Similarity	NPC477574
0.8137	Intermediate Similarity	NPC293753
0.8137	Intermediate Similarity	NPC162973
0.8137	Intermediate Similarity	NPC475344
0.8137	Intermediate Similarity	NPC476471
0.8137	Intermediate Similarity	NPC273668
0.8132	Intermediate Similarity	NPC281880
0.8125	Intermediate Similarity	NPC170633
0.8125	Intermediate Similarity	NPC177141
0.8125	Intermediate Similarity	NPC246028
0.8119	Intermediate Similarity	NPC477968
0.8119	Intermediate Similarity	NPC473510
0.8119	Intermediate Similarity	NPC472826
0.8119	Intermediate Similarity	NPC20113
0.8119	Intermediate Similarity	NPC476767
0.8119	Intermediate Similarity	NPC161527
0.8119	Intermediate Similarity	NPC477972
0.8119	Intermediate Similarity	NPC327431
0.8119	Intermediate Similarity	NPC219285
0.8119	Intermediate Similarity	NPC228251
0.8119	Intermediate Similarity	NPC477971
0.8105	Intermediate Similarity	NPC149224
0.81	Intermediate Similarity	NPC210337
0.81	Intermediate Similarity	NPC73911
0.81	Intermediate Similarity	NPC477719
0.81	Intermediate Similarity	NPC477718
0.8095	Intermediate Similarity	NPC475263
0.8095	Intermediate Similarity	NPC306265
0.8085	Intermediate Similarity	NPC266511
0.8085	Intermediate Similarity	NPC274448
0.8085	Intermediate Similarity	NPC164424
0.8081	Intermediate Similarity	NPC472441
0.8081	Intermediate Similarity	NPC476174
0.8081	Intermediate Similarity	NPC281134
0.8081	Intermediate Similarity	NPC474909
0.8081	Intermediate Similarity	NPC271195
0.8077	Intermediate Similarity	NPC189863
0.8065	Intermediate Similarity	NPC470558
0.8065	Intermediate Similarity	NPC79945
0.8061	Intermediate Similarity	NPC139692
0.8061	Intermediate Similarity	NPC472812
0.8058	Intermediate Similarity	NPC474822
0.8058	Intermediate Similarity	NPC474124
0.8058	Intermediate Similarity	NPC222153
0.8058	Intermediate Similarity	NPC471938
0.8058	Intermediate Similarity	NPC471208
0.8058	Intermediate Similarity	NPC281378
0.8056	Intermediate Similarity	NPC122056
0.8056	Intermediate Similarity	NPC171126
0.8056	Intermediate Similarity	NPC154815
0.8043	Intermediate Similarity	NPC170303
0.8039	Intermediate Similarity	NPC118174
0.8039	Intermediate Similarity	NPC473160
0.8037	Intermediate Similarity	NPC475668

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 NPC218107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1417
0.2-0.3	3658
0.3-0.4	2521
0.4-0.5	904
0.5-0.6	221
0.6-0.7	239
0.7-0.8	21
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8866	High Similarity	NPD7640	Approved
0.8866	High Similarity	NPD7639	Approved
0.8763	High Similarity	NPD7638	Approved
0.8137	Intermediate Similarity	NPD7632	Discontinued
0.802	Intermediate Similarity	NPD4225	Approved
0.7838	Intermediate Similarity	NPD7115	Discovery
0.7742	Intermediate Similarity	NPD7525	Registered
0.7611	Intermediate Similarity	NPD7328	Approved
0.7611	Intermediate Similarity	NPD7327	Approved
0.76	Intermediate Similarity	NPD7515	Phase 2
0.7565	Intermediate Similarity	NPD8033	Approved
0.7544	Intermediate Similarity	NPD7516	Approved
0.7478	Intermediate Similarity	NPD8294	Approved
0.7478	Intermediate Similarity	NPD8377	Approved
0.7451	Intermediate Similarity	NPD7748	Approved
0.7431	Intermediate Similarity	NPD6899	Approved
0.7431	Intermediate Similarity	NPD6881	Approved
0.7426	Intermediate Similarity	NPD6079	Approved
0.7426	Intermediate Similarity	NPD7637	Suspended
0.7414	Intermediate Similarity	NPD8379	Approved
0.7414	Intermediate Similarity	NPD8296	Approved
0.7414	Intermediate Similarity	NPD8378	Approved
0.7414	Intermediate Similarity	NPD8380	Approved
0.7414	Intermediate Similarity	NPD8335	Approved
0.7407	Intermediate Similarity	NPD7128	Approved
0.7407	Intermediate Similarity	NPD6402	Approved
0.7407	Intermediate Similarity	NPD5739	Approved
0.7407	Intermediate Similarity	NPD6675	Approved
0.74	Intermediate Similarity	NPD6051	Approved
0.74	Intermediate Similarity	NPD5328	Approved
0.7374	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5344	Discontinued
0.7353	Intermediate Similarity	NPD6399	Phase 3
0.7347	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5697	Approved
0.732	Intermediate Similarity	NPD6695	Phase 3
0.7311	Intermediate Similarity	NPD7507	Approved
0.7297	Intermediate Similarity	NPD7290	Approved
0.7297	Intermediate Similarity	NPD7102	Approved
0.7297	Intermediate Similarity	NPD6883	Approved
0.729	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7273	Intermediate Similarity	NPD6011	Approved
0.7273	Intermediate Similarity	NPD6686	Approved
0.7273	Intermediate Similarity	NPD7320	Approved
0.7265	Intermediate Similarity	NPD7503	Approved
0.7257	Intermediate Similarity	NPD4632	Approved
0.7245	Intermediate Similarity	NPD4786	Approved
0.7245	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7902	Approved
0.7238	Intermediate Similarity	NPD6083	Phase 2
0.7238	Intermediate Similarity	NPD6084	Phase 2
0.7232	Intermediate Similarity	NPD6617	Approved
0.7232	Intermediate Similarity	NPD6869	Approved
0.7232	Intermediate Similarity	NPD6650	Approved
0.7232	Intermediate Similarity	NPD6847	Approved
0.7232	Intermediate Similarity	NPD6649	Approved
0.7232	Intermediate Similarity	NPD8130	Phase 1
0.7216	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6372	Approved
0.7207	Intermediate Similarity	NPD6373	Approved
0.7207	Intermediate Similarity	NPD6013	Approved
0.7207	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6012	Approved
0.7207	Intermediate Similarity	NPD6014	Approved
0.7204	Intermediate Similarity	NPD7339	Approved
0.7204	Intermediate Similarity	NPD6942	Approved
0.7188	Intermediate Similarity	NPD7332	Phase 2
0.7188	Intermediate Similarity	NPD6931	Approved
0.7188	Intermediate Similarity	NPD6930	Phase 2
0.7184	Intermediate Similarity	NPD4202	Approved
0.7182	Intermediate Similarity	NPD5701	Approved
0.7168	Intermediate Similarity	NPD8297	Approved
0.7168	Intermediate Similarity	NPD6882	Approved
0.7156	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7319	Approved
0.7103	Intermediate Similarity	NPD5285	Approved
0.7103	Intermediate Similarity	NPD5286	Approved
0.7103	Intermediate Similarity	NPD4696	Approved
0.7103	Intermediate Similarity	NPD6648	Approved
0.7091	Intermediate Similarity	NPD6008	Approved
0.7087	Intermediate Similarity	NPD8034	Phase 2
0.7087	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD7645	Phase 2
0.7083	Intermediate Similarity	NPD6929	Approved
0.708	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4755	Approved
0.7075	Intermediate Similarity	NPD5173	Approved
0.7069	Intermediate Similarity	NPD6009	Approved
0.7041	Intermediate Similarity	NPD3667	Approved
0.7037	Intermediate Similarity	NPD5223	Approved
0.703	Intermediate Similarity	NPD7524	Approved
0.703	Intermediate Similarity	NPD7750	Discontinued
0.7018	Intermediate Similarity	NPD6053	Discontinued
0.701	Intermediate Similarity	NPD7514	Phase 3
0.6991	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5785	Approved
0.6981	Remote Similarity	NPD4697	Phase 3
0.6979	Remote Similarity	NPD6114	Approved
0.6979	Remote Similarity	NPD6115	Approved
0.6979	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6697	Approved
0.6979	Remote Similarity	NPD6118	Approved
0.6972	Remote Similarity	NPD4633	Approved
0.6972	Remote Similarity	NPD5224	Approved
0.6972	Remote Similarity	NPD5225	Approved
0.6972	Remote Similarity	NPD5226	Approved
0.6961	Remote Similarity	NPD5737	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6672	Approved
0.6952	Remote Similarity	NPD7900	Approved
0.6952	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4700	Approved
0.6939	Remote Similarity	NPD6898	Phase 1
0.6931	Remote Similarity	NPD7521	Approved
0.6931	Remote Similarity	NPD7334	Approved
0.6931	Remote Similarity	NPD6684	Approved
0.6931	Remote Similarity	NPD6409	Approved
0.6931	Remote Similarity	NPD7146	Approved
0.6931	Remote Similarity	NPD5330	Approved
0.6923	Remote Similarity	NPD5693	Phase 1
0.6915	Remote Similarity	NPD6924	Approved
0.6915	Remote Similarity	NPD6926	Approved
0.6909	Remote Similarity	NPD5174	Approved
0.6909	Remote Similarity	NPD5175	Approved
0.6907	Remote Similarity	NPD4195	Approved
0.69	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3665	Phase 1
0.69	Remote Similarity	NPD3133	Approved
0.69	Remote Similarity	NPD3666	Approved
0.6893	Remote Similarity	NPD4753	Phase 2
0.6891	Remote Similarity	NPD6319	Approved
0.6887	Remote Similarity	NPD5695	Phase 3
0.6887	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6925	Approved
0.6875	Remote Similarity	NPD5776	Phase 2
0.6864	Remote Similarity	NPD6335	Approved
0.686	Remote Similarity	NPD7604	Phase 2
0.6852	Remote Similarity	NPD5696	Approved
0.6842	Remote Similarity	NPD6371	Approved
0.6842	Remote Similarity	NPD4634	Approved
0.6838	Remote Similarity	NPD6274	Approved
0.6838	Remote Similarity	NPD6868	Approved
0.6837	Remote Similarity	NPD7509	Discontinued
0.6833	Remote Similarity	NPD5983	Phase 2
0.6832	Remote Similarity	NPD1694	Approved
0.6832	Remote Similarity	NPD6893	Approved
0.6807	Remote Similarity	NPD7101	Approved
0.6807	Remote Similarity	NPD7100	Approved
0.6804	Remote Similarity	NPD7145	Approved
0.6803	Remote Similarity	NPD7492	Approved
0.68	Remote Similarity	NPD5362	Discontinued
0.68	Remote Similarity	NPD4788	Approved
0.6796	Remote Similarity	NPD6903	Approved
0.678	Remote Similarity	NPD6317	Approved
0.6774	Remote Similarity	NPD7736	Approved
0.6771	Remote Similarity	NPD6933	Approved
0.6771	Remote Similarity	NPD6117	Approved
0.6768	Remote Similarity	NPD6902	Approved
0.6765	Remote Similarity	NPD4623	Approved
0.6765	Remote Similarity	NPD4519	Discontinued
0.6765	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7087	Discontinued
0.6757	Remote Similarity	NPD4754	Approved
0.675	Remote Similarity	NPD6054	Approved
0.6748	Remote Similarity	NPD6336	Discontinued
0.6748	Remote Similarity	NPD6616	Approved
0.6731	Remote Similarity	NPD6904	Approved
0.6731	Remote Similarity	NPD6673	Approved
0.6731	Remote Similarity	NPD6080	Approved
0.6729	Remote Similarity	NPD5210	Approved
0.6729	Remote Similarity	NPD4629	Approved
0.6726	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6313	Approved
0.6723	Remote Similarity	NPD6314	Approved
0.6701	Remote Similarity	NPD6116	Phase 1
0.6701	Remote Similarity	NPD6932	Approved
0.67	Remote Similarity	NPD4221	Approved
0.67	Remote Similarity	NPD4223	Phase 3
0.6699	Remote Similarity	NPD3573	Approved
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6697	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD5329	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6637	Remote Similarity	NPD4768	Approved
0.6637	Remote Similarity	NPD4767	Approved
0.6633	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6059	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data