NPASS Compound

Structure

CID160056 OpenBabel06191715532D 34 38 0 0 1 0 0 0 0 0999 V2000 1.8862 -3.1656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7777 -5.3545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9803 -4.3998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 2.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5662 2.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6928 -1.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6920 1.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7012 -6.3553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7956 -3.5709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4938 -2.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3836 -0.9754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7504 -3.7736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3833 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 -1.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 -0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -2.4401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5388 -1.4642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8457 1.4657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8465 1.4652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5376 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8460 0.4887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0522 -4.7017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6925 -0.9759 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6922 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8463 0.4882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7116 1.9660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4038 1.9644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3994 -5.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 8 34 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 30 1 0 0 0 0 19 31 1 0 0 0 0 20 1 1 1 0 0 0 20 21 1 0 0 0 0 21 28 1 6 0 0 0 22 25 1 0 0 0 0 22 32 1 6 0 0 0 23 27 1 0 0 0 0 23 30 1 6 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 25 29 1 1 0 0 0 25 31 1 0 0 0 0 26 34 1 0 0 0 0 28 29 1 6 0 0 0 29 7 1 1 0 0 0 30 31 1 1 0 0 0 31 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.38
Volume:	523.047
LogP:	6.079
LogD:	5.069
LogS:	-5.597
# Rotatable Bonds:	5
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	5.879
Fsp3:	0.903
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.099
MDCK Permeability:	1.550823071738705e-05
Pgp-inhibitor:	0.599
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.348
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272
Plasma Protein Binding (PPB):	95.65219116210938%
Volume Distribution (VD):	1.161
Pgp-substrate:	3.286813974380493%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.663
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.26
CYP2C9-substrate:	0.454
CYP2D6-inhibitor:	0.167
CYP2D6-substrate:	0.571
CYP3A4-inhibitor:	0.945
CYP3A4-substrate:	0.78

ADMET: Excretion

Clearance (CL):	5.841
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.153
Human Hepatotoxicity (H-HT):	0.452
Drug-inuced Liver Injury (DILI):	0.099
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.922
Carcinogencity:	0.329
Eye Corrosion:	0.021
Eye Irritation:	0.04
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC160056

Natural Product ID:	NPC160056
*Common Name:**	Combretanone G
IUPAC Name:	n.a.
Synonyms:	Combretanone G
Standard InCHIKey:	PSQJXRKLAZZNHC-OLKLHFONSA-N
Standard InCHI:	InChI=1S/C31H50O3/c1-20(10-9-13-26(2,3)34-8)21-11-14-29(7)25-22(32)18-23-27(4,5)24(33)12-15-30(23)19-31(25,30)17-16-28(21,29)6/h9,13,20-23,25,32H,10-12,14-19H2,1-8H3/b13-9+/t20-,21-,22+,23+,25+,28-,29+,30-,31+/m1/s1
SMILES:	COC(/C=C/C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2[C@@H](O)C[C@@H]2[C@]3(C1)CCC(=O)C2(C)C)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689266
PubChem CID:	51041526
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3892	Individual Protein	Tumor necrosis factor receptor superfamily member 10B	Homo sapiens	FC	=	2.5	n.a.	PMID[490603]

☑ 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 NPC160056 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	197
0.1-0.2	1301
0.2-0.3	4760
0.3-0.4	12827
0.4-0.5	9814
0.5-0.6	6321
0.6-0.7	5507
0.7-0.8	1881
0.8-0.85	77
0.85-0.9	11
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC263729
0.8652	High Similarity	NPC470558
0.8632	High Similarity	NPC84383
0.8632	High Similarity	NPC259286
0.8587	High Similarity	NPC193360
0.8542	High Similarity	NPC249954
0.8511	High Similarity	NPC475806
0.8511	High Similarity	NPC472975
0.85	High Similarity	NPC201763
0.8485	Intermediate Similarity	NPC185530
0.8454	Intermediate Similarity	NPC126815
0.8454	Intermediate Similarity	NPC291634
0.8444	Intermediate Similarity	NPC134481
0.8444	Intermediate Similarity	NPC82623
0.8431	Intermediate Similarity	NPC163216
0.8421	Intermediate Similarity	NPC69454
0.8421	Intermediate Similarity	NPC12722
0.84	Intermediate Similarity	NPC26478
0.8387	Intermediate Similarity	NPC328539
0.8384	Intermediate Similarity	NPC476897
0.8352	Intermediate Similarity	NPC470077
0.8351	Intermediate Similarity	NPC78473
0.835	Intermediate Similarity	NPC257082
0.835	Intermediate Similarity	NPC285298
0.8333	Intermediate Similarity	NPC8993
0.8316	Intermediate Similarity	NPC63748
0.8316	Intermediate Similarity	NPC272746
0.8298	Intermediate Similarity	NPC2983
0.8298	Intermediate Similarity	NPC275740
0.8298	Intermediate Similarity	NPC473999
0.8298	Intermediate Similarity	NPC128496
0.8298	Intermediate Similarity	NPC309603
0.8298	Intermediate Similarity	NPC86319
0.8283	Intermediate Similarity	NPC201406
0.828	Intermediate Similarity	NPC4643
0.8261	Intermediate Similarity	NPC471224
0.8261	Intermediate Similarity	NPC202868
0.8261	Intermediate Similarity	NPC22133
0.8261	Intermediate Similarity	NPC76518
0.8247	Intermediate Similarity	NPC271195
0.8242	Intermediate Similarity	NPC470046
0.8242	Intermediate Similarity	NPC470047
0.8235	Intermediate Similarity	NPC60681
0.8229	Intermediate Similarity	NPC477855
0.8229	Intermediate Similarity	NPC477520
0.8218	Intermediate Similarity	NPC112009
0.8211	Intermediate Similarity	NPC48010
0.8211	Intermediate Similarity	NPC320026
0.8211	Intermediate Similarity	NPC126993
0.8191	Intermediate Similarity	NPC143767
0.8191	Intermediate Similarity	NPC131470
0.8191	Intermediate Similarity	NPC53911
0.8182	Intermediate Similarity	NPC124703
0.8182	Intermediate Similarity	NPC57079
0.8182	Intermediate Similarity	NPC477854
0.8182	Intermediate Similarity	NPC108368
0.8182	Intermediate Similarity	NPC234617
0.8155	Intermediate Similarity	NPC144459
0.8155	Intermediate Similarity	NPC475294
0.8152	Intermediate Similarity	NPC59453
0.8152	Intermediate Similarity	NPC221758
0.8144	Intermediate Similarity	NPC209662
0.8144	Intermediate Similarity	NPC299100
0.8144	Intermediate Similarity	NPC292793
0.8132	Intermediate Similarity	NPC296701
0.8132	Intermediate Similarity	NPC218616
0.8132	Intermediate Similarity	NPC477858
0.8132	Intermediate Similarity	NPC470049
0.8125	Intermediate Similarity	NPC168027
0.8125	Intermediate Similarity	NPC185936
0.8125	Intermediate Similarity	NPC473998
0.8119	Intermediate Similarity	NPC477915
0.8111	Intermediate Similarity	NPC164999
0.8105	Intermediate Similarity	NPC122116
0.8105	Intermediate Similarity	NPC474245
0.8105	Intermediate Similarity	NPC472973
0.8105	Intermediate Similarity	NPC32830
0.81	Intermediate Similarity	NPC117685
0.81	Intermediate Similarity	NPC112167
0.8085	Intermediate Similarity	NPC58063
0.8085	Intermediate Similarity	NPC475740
0.8085	Intermediate Similarity	NPC57469
0.8085	Intermediate Similarity	NPC474684
0.8085	Intermediate Similarity	NPC141292
0.8085	Intermediate Similarity	NPC142361
0.8081	Intermediate Similarity	NPC151488
0.8081	Intermediate Similarity	NPC190554
0.8081	Intermediate Similarity	NPC253826
0.8077	Intermediate Similarity	NPC177064
0.8065	Intermediate Similarity	NPC470574
0.8065	Intermediate Similarity	NPC292553
0.8065	Intermediate Similarity	NPC474083
0.8065	Intermediate Similarity	NPC157257
0.8065	Intermediate Similarity	NPC274448
0.8065	Intermediate Similarity	NPC137493
0.8061	Intermediate Similarity	NPC476174
0.8061	Intermediate Similarity	NPC279974
0.8061	Intermediate Similarity	NPC180950
0.8058	Intermediate Similarity	NPC478052
0.8058	Intermediate Similarity	NPC189863
0.8043	Intermediate Similarity	NPC475726
0.8043	Intermediate Similarity	NPC476082
0.8043	Intermediate Similarity	NPC472743
0.8043	Intermediate Similarity	NPC278648
0.8041	Intermediate Similarity	NPC472930
0.8039	Intermediate Similarity	NPC476237
0.8039	Intermediate Similarity	NPC180204
0.8039	Intermediate Similarity	NPC222153
0.8039	Intermediate Similarity	NPC36688
0.8039	Intermediate Similarity	NPC312900
0.8037	Intermediate Similarity	NPC73050
0.8021	Intermediate Similarity	NPC183283
0.8021	Intermediate Similarity	NPC85173
0.802	Intermediate Similarity	NPC477052
0.802	Intermediate Similarity	NPC477053
0.802	Intermediate Similarity	NPC235142
0.802	Intermediate Similarity	NPC477051
0.8	Intermediate Similarity	NPC103051
0.8	Intermediate Similarity	NPC215843
0.8	Intermediate Similarity	NPC292491
0.8	Intermediate Similarity	NPC191565
0.8	Intermediate Similarity	NPC310752
0.8	Intermediate Similarity	NPC471722
0.8	Intermediate Similarity	NPC98868
0.7981	Intermediate Similarity	NPC131665
0.7981	Intermediate Similarity	NPC255387
0.798	Intermediate Similarity	NPC477853
0.798	Intermediate Similarity	NPC327788
0.7979	Intermediate Similarity	NPC31564
0.7979	Intermediate Similarity	NPC470051
0.7979	Intermediate Similarity	NPC474733
0.7979	Intermediate Similarity	NPC72133
0.7979	Intermediate Similarity	NPC94755
0.7979	Intermediate Similarity	NPC469994
0.7979	Intermediate Similarity	NPC472738
0.7979	Intermediate Similarity	NPC474732
0.7979	Intermediate Similarity	NPC474778
0.7979	Intermediate Similarity	NPC145879
0.7979	Intermediate Similarity	NPC51014
0.7979	Intermediate Similarity	NPC470050
0.7978	Intermediate Similarity	NPC472746
0.7978	Intermediate Similarity	NPC470557
0.7961	Intermediate Similarity	NPC72255
0.7961	Intermediate Similarity	NPC209502
0.7961	Intermediate Similarity	NPC29705
0.7961	Intermediate Similarity	NPC204833
0.7959	Intermediate Similarity	NPC91010
0.7959	Intermediate Similarity	NPC471207
0.7959	Intermediate Similarity	NPC474690
0.7959	Intermediate Similarity	NPC201725
0.7957	Intermediate Similarity	NPC82902
0.7957	Intermediate Similarity	NPC475745
0.7957	Intermediate Similarity	NPC85774
0.7957	Intermediate Similarity	NPC146683
0.7957	Intermediate Similarity	NPC474482
0.7957	Intermediate Similarity	NPC227132
0.7957	Intermediate Similarity	NPC214043
0.7941	Intermediate Similarity	NPC477054
0.7941	Intermediate Similarity	NPC193934
0.7941	Intermediate Similarity	NPC155332
0.7941	Intermediate Similarity	NPC136289
0.7941	Intermediate Similarity	NPC32577
0.7941	Intermediate Similarity	NPC114540
0.7941	Intermediate Similarity	NPC271980
0.7941	Intermediate Similarity	NPC473424
0.7938	Intermediate Similarity	NPC233116
0.7938	Intermediate Similarity	NPC110923
0.7938	Intermediate Similarity	NPC472978
0.7938	Intermediate Similarity	NPC262870
0.7938	Intermediate Similarity	NPC74296
0.7935	Intermediate Similarity	NPC145143
0.7935	Intermediate Similarity	NPC151519
0.7925	Intermediate Similarity	NPC76084
0.7921	Intermediate Similarity	NPC154072
0.7921	Intermediate Similarity	NPC477521
0.7921	Intermediate Similarity	NPC144956
0.7921	Intermediate Similarity	NPC476303
0.7921	Intermediate Similarity	NPC83709
0.7921	Intermediate Similarity	NPC473176
0.7921	Intermediate Similarity	NPC15390
0.7917	Intermediate Similarity	NPC475921
0.7917	Intermediate Similarity	NPC69627
0.7917	Intermediate Similarity	NPC186688
0.7917	Intermediate Similarity	NPC472970
0.7917	Intermediate Similarity	NPC229871
0.7917	Intermediate Similarity	NPC76879
0.7917	Intermediate Similarity	NPC31985
0.7917	Intermediate Similarity	NPC472971
0.7917	Intermediate Similarity	NPC1015
0.7917	Intermediate Similarity	NPC469319
0.7917	Intermediate Similarity	NPC474704
0.79	Intermediate Similarity	NPC107243
0.79	Intermediate Similarity	NPC57416
0.79	Intermediate Similarity	NPC18509
0.79	Intermediate Similarity	NPC474938
0.79	Intermediate Similarity	NPC474785
0.7895	Intermediate Similarity	NPC187376
0.7895	Intermediate Similarity	NPC233836
0.7895	Intermediate Similarity	NPC317590
0.7895	Intermediate Similarity	NPC93778

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 NPC160056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1514
0.2-0.3	4042
0.3-0.4	2336
0.4-0.5	631
0.5-0.6	169
0.6-0.7	183
0.7-0.8	111
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8511	High Similarity	NPD6079	Approved
0.8495	Intermediate Similarity	NPD5328	Approved
0.8152	Intermediate Similarity	NPD4786	Approved
0.798	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD5222	Approved
0.798	Intermediate Similarity	NPD5221	Approved
0.7979	Intermediate Similarity	NPD3618	Phase 1
0.7941	Intermediate Similarity	NPD5211	Phase 2
0.7935	Intermediate Similarity	NPD3667	Approved
0.7921	Intermediate Similarity	NPD5285	Approved
0.7921	Intermediate Similarity	NPD5286	Approved
0.7921	Intermediate Similarity	NPD4696	Approved
0.79	Intermediate Similarity	NPD5173	Approved
0.79	Intermediate Similarity	NPD4755	Approved
0.7857	Intermediate Similarity	NPD4202	Approved
0.7843	Intermediate Similarity	NPD5223	Approved
0.7822	Intermediate Similarity	NPD7638	Approved
0.78	Intermediate Similarity	NPD4697	Phase 3
0.7788	Intermediate Similarity	NPD5141	Approved
0.7767	Intermediate Similarity	NPD5224	Approved
0.7767	Intermediate Similarity	NPD4633	Approved
0.7767	Intermediate Similarity	NPD5226	Approved
0.7767	Intermediate Similarity	NPD5225	Approved
0.7745	Intermediate Similarity	NPD4700	Approved
0.7745	Intermediate Similarity	NPD7640	Approved
0.7745	Intermediate Similarity	NPD7639	Approved
0.7736	Intermediate Similarity	NPD6899	Approved
0.7736	Intermediate Similarity	NPD6881	Approved
0.7717	Intermediate Similarity	NPD7525	Registered
0.7714	Intermediate Similarity	NPD5739	Approved
0.7714	Intermediate Similarity	NPD7128	Approved
0.7714	Intermediate Similarity	NPD6675	Approved
0.7714	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD5174	Approved
0.7692	Intermediate Similarity	NPD5175	Approved
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7115	Discovery
0.7642	Intermediate Similarity	NPD5697	Approved
0.7593	Intermediate Similarity	NPD7290	Approved
0.7593	Intermediate Similarity	NPD7102	Approved
0.7593	Intermediate Similarity	NPD6883	Approved
0.7579	Intermediate Similarity	NPD3666	Approved
0.7579	Intermediate Similarity	NPD3133	Approved
0.7579	Intermediate Similarity	NPD3665	Phase 1
0.757	Intermediate Similarity	NPD6011	Approved
0.757	Intermediate Similarity	NPD7320	Approved
0.7524	Intermediate Similarity	NPD4754	Approved
0.7523	Intermediate Similarity	NPD6617	Approved
0.7523	Intermediate Similarity	NPD6650	Approved
0.7523	Intermediate Similarity	NPD8130	Phase 1
0.7523	Intermediate Similarity	NPD6869	Approved
0.7523	Intermediate Similarity	NPD6649	Approved
0.7523	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7474	Intermediate Similarity	NPD4788	Approved
0.7455	Intermediate Similarity	NPD8297	Approved
0.7455	Intermediate Similarity	NPD6882	Approved
0.7416	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4730	Approved
0.7407	Intermediate Similarity	NPD4729	Approved
0.74	Intermediate Similarity	NPD7515	Phase 2
0.7383	Intermediate Similarity	NPD4767	Approved
0.7383	Intermediate Similarity	NPD4768	Approved
0.7374	Intermediate Similarity	NPD4753	Phase 2
0.7368	Intermediate Similarity	NPD4221	Approved
0.7368	Intermediate Similarity	NPD4223	Phase 3
0.7364	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3703	Phase 2
0.732	Intermediate Similarity	NPD5329	Approved
0.7273	Intermediate Similarity	NPD5247	Approved
0.7273	Intermediate Similarity	NPD5249	Phase 3
0.7273	Intermediate Similarity	NPD5248	Approved
0.7273	Intermediate Similarity	NPD5135	Approved
0.7273	Intermediate Similarity	NPD5169	Approved
0.7273	Intermediate Similarity	NPD5251	Approved
0.7273	Intermediate Similarity	NPD5250	Approved
0.7273	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7748	Approved
0.7248	Intermediate Similarity	NPD5168	Approved
0.7248	Intermediate Similarity	NPD5128	Approved
0.7245	Intermediate Similarity	NPD5279	Phase 3
0.7232	Intermediate Similarity	NPD4632	Approved
0.7228	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD8035	Phase 2
0.7216	Intermediate Similarity	NPD3668	Phase 3
0.7216	Intermediate Similarity	NPD4197	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7207	Intermediate Similarity	NPD5217	Approved
0.7207	Intermediate Similarity	NPD5216	Approved
0.7207	Intermediate Similarity	NPD5215	Approved
0.7207	Intermediate Similarity	NPD5127	Approved
0.7191	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5210	Approved
0.7184	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4629	Approved
0.7174	Intermediate Similarity	NPD6942	Approved
0.7174	Intermediate Similarity	NPD7339	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD6335	Approved
0.7128	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7604	Phase 2
0.7105	Intermediate Similarity	NPD6868	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.71	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6117	Approved
0.7079	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5360	Phase 3
0.7071	Intermediate Similarity	NPD4688	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD4693	Phase 3
0.7071	Intermediate Similarity	NPD4689	Approved
0.7071	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4623	Approved
0.7071	Intermediate Similarity	NPD4690	Approved
0.7071	Intermediate Similarity	NPD5205	Approved
0.7071	Intermediate Similarity	NPD4138	Approved
0.7071	Intermediate Similarity	NPD4519	Discontinued
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7071	Intermediate Similarity	NPD5690	Phase 2
0.7069	Intermediate Similarity	NPD7100	Approved
0.7069	Intermediate Similarity	NPD7101	Approved
0.7065	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6008	Approved
0.7053	Intermediate Similarity	NPD7645	Phase 2
0.7048	Intermediate Similarity	NPD7902	Approved
0.7043	Intermediate Similarity	NPD6009	Approved
0.7043	Intermediate Similarity	NPD6317	Approved
0.7021	Intermediate Similarity	NPD6116	Phase 1
0.7018	Intermediate Similarity	NPD5167	Approved
0.7009	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD3573	Approved
0.6983	Remote Similarity	NPD6313	Approved
0.6983	Remote Similarity	NPD6314	Approved
0.6967	Remote Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD6274	Approved
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6937	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD5737	Approved
0.6923	Remote Similarity	NPD4244	Approved
0.6923	Remote Similarity	NPD6001	Approved
0.6923	Remote Similarity	NPD4789	Approved
0.6923	Remote Similarity	NPD4245	Approved
0.6915	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4694	Approved
0.69	Remote Similarity	NPD5280	Approved
0.69	Remote Similarity	NPD6098	Approved
0.6893	Remote Similarity	NPD5693	Phase 1
0.6891	Remote Similarity	NPD6370	Approved
0.6882	Remote Similarity	NPD6926	Approved
0.6882	Remote Similarity	NPD6924	Approved
0.6875	Remote Similarity	NPD4195	Approved
0.6864	Remote Similarity	NPD6319	Approved
0.6864	Remote Similarity	NPD6059	Approved
0.6863	Remote Similarity	NPD6051	Approved
0.6857	Remote Similarity	NPD5695	Phase 3
0.6832	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5696	Approved
0.6813	Remote Similarity	NPD3698	Phase 2
0.6807	Remote Similarity	NPD6016	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6807	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6908	Approved
0.6807	Remote Similarity	NPD6909	Approved
0.6807	Remote Similarity	NPD6015	Approved
0.68	Remote Similarity	NPD1694	Approved
0.6796	Remote Similarity	NPD5785	Approved
0.6777	Remote Similarity	NPD7492	Approved
0.6771	Remote Similarity	NPD3617	Approved
0.6762	Remote Similarity	NPD7900	Approved
0.6762	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5988	Approved
0.6748	Remote Similarity	NPD7736	Approved
0.6742	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6933	Approved
0.6735	Remote Similarity	NPD6902	Approved
0.6735	Remote Similarity	NPD4692	Approved
0.6735	Remote Similarity	NPD4139	Approved
0.6733	Remote Similarity	NPD5786	Approved
0.6731	Remote Similarity	NPD6411	Approved
0.6731	Remote Similarity	NPD5281	Approved
0.6731	Remote Similarity	NPD5284	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