NPASS Compound

Structure

NPC472434 OpenBabel07101719512D 38 43 0 0 1 0 0 0 0 0999 V2000 -5.2705 -1.6074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2651 -1.7120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8638 -0.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8528 -0.9030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9075 2.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5278 2.2246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 -2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4516 0.1151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4461 0.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 3.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5035 1.4119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 2.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 1.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6456 1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2437 3.0933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8528 0.9241 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 4.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8736 -3.1915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3910 0.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 3.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -2.1970 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 -3.5116 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 11 2 0 0 0 0 4 13 2 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 16 1 0 0 0 0 7 14 1 0 0 0 0 7 26 2 0 0 0 0 8 28 1 0 0 0 0 9 25 1 0 0 0 0 9 29 1 0 0 0 0 10 25 1 0 0 0 0 10 35 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 17 2 0 0 0 0 14 36 1 0 0 0 0 15 8 1 6 0 0 0 15 19 1 0 0 0 0 15 37 1 0 0 0 0 16 27 1 0 0 0 0 16 30 2 0 0 0 0 17 18 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 31 1 1 0 0 0 20 21 1 0 0 0 0 20 32 1 6 0 0 0 21 23 1 0 0 0 0 21 38 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 1 0 0 0 22 33 1 0 0 0 0 23 36 1 6 0 0 0 23 37 1 0 0 0 0 24 35 1 0 0 0 0 24 38 1 6 0 0 0 25 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.15
Volume:	487.212
LogP:	-0.17
LogD:	-0.268
LogS:	-4.351
# Rotatable Bonds:	6
TPSA:	192.67
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.162
Synthetic Accessibility Score:	4.739
Fsp3:	0.44
Lipinski Rule-of-5:	Rejected
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:	-6.344
MDCK Permeability:	7.640578587597702e-06
Pgp-inhibitor:	0.053
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	0.369
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.313
Plasma Protein Binding (PPB):	73.66097259521484%
Volume Distribution (VD):	0.523
Pgp-substrate:	14.930729866027832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.39
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	1.429
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.824
AMES Toxicity:	0.352
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.068
Carcinogencity:	0.928
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.094

Download Data

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

Natural Product: NPC472434

Natural Product ID:	NPC472434
*Common Name:**	XGGJLRIJRXMGJK-LEHRWSAJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XGGJLRIJRXMGJK-LEHRWSAJSA-N
Standard InCHI:	InChI=1S/C25H26N2O11/c28-8-15-19(31)20(32)21(38-24-22(33)25(34,9-29)10-35-24)23(37-15)36-14-7-26-12-5-6-16(30)27-13-4-2-1-3-11(13)17(14)18(12)27/h1-7,15,19-24,28-29,31-34H,8-10H2/t15-,19-,20+,21-,22+,23-,24+,25-/m1/s1
SMILES:	C1C(C(C(O1)OC2C(C(C(OC2OC3=CN=C4C=CC(=O)N5C4=C3C6=CC=CC=C65)CO)O)O)O)(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3403680
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003805] Indolonaphthyridine alkaloids

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	63500.0	nM	PMID[448154]

☑ 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 NPC472434 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	568
0.1-0.2	2266
0.2-0.3	9914
0.3-0.4	9937
0.4-0.5	14072
0.5-0.6	4133
0.6-0.7	1639
0.7-0.8	160
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9513	High Similarity	NPC472436
0.9467	High Similarity	NPC472435
0.9148	High Similarity	NPC99891
0.8472	Intermediate Similarity	NPC287208
0.8206	Intermediate Similarity	NPC288349
0.8069	Intermediate Similarity	NPC141053
0.7937	Intermediate Similarity	NPC174672
0.786	Intermediate Similarity	NPC26543
0.7857	Intermediate Similarity	NPC174758
0.7812	Intermediate Similarity	NPC82548
0.7808	Intermediate Similarity	NPC239954
0.7788	Intermediate Similarity	NPC198673
0.7763	Intermediate Similarity	NPC267928
0.7727	Intermediate Similarity	NPC168911
0.7686	Intermediate Similarity	NPC124300
0.7664	Intermediate Similarity	NPC310618
0.7654	Intermediate Similarity	NPC291609
0.7652	Intermediate Similarity	NPC274982
0.7647	Intermediate Similarity	NPC212213
0.7647	Intermediate Similarity	NPC469554
0.7634	Intermediate Similarity	NPC200836
0.76	Intermediate Similarity	NPC258048
0.7598	Intermediate Similarity	NPC26679
0.7578	Intermediate Similarity	NPC19872
0.7556	Intermediate Similarity	NPC53144
0.7553	Intermediate Similarity	NPC110151
0.7545	Intermediate Similarity	NPC226202
0.7544	Intermediate Similarity	NPC477548
0.7521	Intermediate Similarity	NPC314954
0.7511	Intermediate Similarity	NPC211813
0.75	Intermediate Similarity	NPC308392
0.75	Intermediate Similarity	NPC8022
0.75	Intermediate Similarity	NPC101543
0.75	Intermediate Similarity	NPC470799
0.7467	Intermediate Similarity	NPC185782
0.7467	Intermediate Similarity	NPC469589
0.7447	Intermediate Similarity	NPC128115
0.7445	Intermediate Similarity	NPC264166
0.7445	Intermediate Similarity	NPC274291
0.7445	Intermediate Similarity	NPC329708
0.7445	Intermediate Similarity	NPC118832
0.7445	Intermediate Similarity	NPC47059
0.7445	Intermediate Similarity	NPC165349
0.7414	Intermediate Similarity	NPC476287
0.7412	Intermediate Similarity	NPC472111
0.7412	Intermediate Similarity	NPC471736
0.7401	Intermediate Similarity	NPC475774
0.74	Intermediate Similarity	NPC473800
0.7362	Intermediate Similarity	NPC469594
0.7359	Intermediate Similarity	NPC85273
0.7342	Intermediate Similarity	NPC310118
0.7309	Intermediate Similarity	NPC79293
0.7309	Intermediate Similarity	NPC279401
0.7296	Intermediate Similarity	NPC96405
0.7296	Intermediate Similarity	NPC171409
0.7293	Intermediate Similarity	NPC470500
0.7265	Intermediate Similarity	NPC74562
0.7265	Intermediate Similarity	NPC57453
0.7265	Intermediate Similarity	NPC151781
0.7265	Intermediate Similarity	NPC316181
0.7256	Intermediate Similarity	NPC196449
0.7256	Intermediate Similarity	NPC314222
0.7249	Intermediate Similarity	NPC245816
0.7249	Intermediate Similarity	NPC476138
0.7248	Intermediate Similarity	NPC219963
0.7248	Intermediate Similarity	NPC152620
0.7229	Intermediate Similarity	NPC135549
0.7224	Intermediate Similarity	NPC182222
0.7222	Intermediate Similarity	NPC296482
0.7222	Intermediate Similarity	NPC165964
0.7222	Intermediate Similarity	NPC53069
0.7222	Intermediate Similarity	NPC202768
0.7218	Intermediate Similarity	NPC148889
0.7216	Intermediate Similarity	NPC53534
0.7211	Intermediate Similarity	NPC161801
0.7206	Intermediate Similarity	NPC474183
0.7191	Intermediate Similarity	NPC471080
0.7191	Intermediate Similarity	NPC469592
0.7185	Intermediate Similarity	NPC193267
0.7185	Intermediate Similarity	NPC213530
0.716	Intermediate Similarity	NPC316224
0.7155	Intermediate Similarity	NPC313189
0.7154	Intermediate Similarity	NPC253675
0.7149	Intermediate Similarity	NPC20249
0.7149	Intermediate Similarity	NPC62510
0.7143	Intermediate Similarity	NPC196718
0.7137	Intermediate Similarity	NPC470785
0.7137	Intermediate Similarity	NPC5145
0.7123	Intermediate Similarity	NPC24864
0.7113	Intermediate Similarity	NPC313804
0.7113	Intermediate Similarity	NPC315804
0.7112	Intermediate Similarity	NPC474145
0.7112	Intermediate Similarity	NPC238457
0.7112	Intermediate Similarity	NPC475841
0.7097	Intermediate Similarity	NPC184680
0.7091	Intermediate Similarity	NPC266551
0.7091	Intermediate Similarity	NPC161887
0.7078	Intermediate Similarity	NPC12649
0.7076	Intermediate Similarity	NPC244856
0.7076	Intermediate Similarity	NPC203168
0.7074	Intermediate Similarity	NPC160127
0.7074	Intermediate Similarity	NPC50997
0.7073	Intermediate Similarity	NPC102593
0.7071	Intermediate Similarity	NPC174788
0.7068	Intermediate Similarity	NPC470784
0.7064	Intermediate Similarity	NPC123976
0.7064	Intermediate Similarity	NPC219664
0.7064	Intermediate Similarity	NPC167860
0.7061	Intermediate Similarity	NPC476998
0.7061	Intermediate Similarity	NPC476996
0.7056	Intermediate Similarity	NPC311357
0.7056	Intermediate Similarity	NPC295898
0.7054	Intermediate Similarity	NPC60621
0.7049	Intermediate Similarity	NPC186351
0.7046	Intermediate Similarity	NPC306644
0.7046	Intermediate Similarity	NPC236424
0.7043	Intermediate Similarity	NPC234197
0.7037	Intermediate Similarity	NPC473449
0.7037	Intermediate Similarity	NPC212766
0.7037	Intermediate Similarity	NPC289423
0.7028	Intermediate Similarity	NPC476995
0.7024	Intermediate Similarity	NPC477806
0.7024	Intermediate Similarity	NPC477805
0.7024	Intermediate Similarity	NPC477796
0.7024	Intermediate Similarity	NPC75179
0.7024	Intermediate Similarity	NPC477795
0.702	Intermediate Similarity	NPC476997
0.702	Intermediate Similarity	NPC476994
0.7017	Intermediate Similarity	NPC274842
0.7017	Intermediate Similarity	NPC153452
0.7013	Intermediate Similarity	NPC232727
0.7012	Intermediate Similarity	NPC132642
0.7011	Intermediate Similarity	NPC328928
0.7009	Intermediate Similarity	NPC328798
0.7009	Intermediate Similarity	NPC474905
0.7004	Intermediate Similarity	NPC264176
0.7004	Intermediate Similarity	NPC314882
0.7004	Intermediate Similarity	NPC202605
0.7004	Intermediate Similarity	NPC112206
0.7	Intermediate Similarity	NPC82070
0.7	Intermediate Similarity	NPC314270
0.6996	Remote Similarity	NPC227824
0.6996	Remote Similarity	NPC285558
0.6996	Remote Similarity	NPC475271
0.6991	Remote Similarity	NPC127647
0.6988	Remote Similarity	NPC477549
0.6983	Remote Similarity	NPC90019
0.6982	Remote Similarity	NPC325093
0.6977	Remote Similarity	NPC478045
0.6972	Remote Similarity	NPC471614
0.6971	Remote Similarity	NPC46451
0.697	Remote Similarity	NPC176538
0.697	Remote Similarity	NPC477019
0.6969	Remote Similarity	NPC58209
0.6966	Remote Similarity	NPC309498
0.6964	Remote Similarity	NPC476999
0.6964	Remote Similarity	NPC260434
0.6962	Remote Similarity	NPC478006
0.6953	Remote Similarity	NPC476115
0.6944	Remote Similarity	NPC81175
0.6941	Remote Similarity	NPC471891
0.6936	Remote Similarity	NPC193238
0.6933	Remote Similarity	NPC111732
0.6933	Remote Similarity	NPC325775
0.6933	Remote Similarity	NPC472098
0.6932	Remote Similarity	NPC315467
0.693	Remote Similarity	NPC84853
0.6929	Remote Similarity	NPC23614
0.6929	Remote Similarity	NPC197141
0.6929	Remote Similarity	NPC100079
0.6926	Remote Similarity	NPC18487
0.6923	Remote Similarity	NPC16452
0.6923	Remote Similarity	NPC476581
0.6923	Remote Similarity	NPC36229
0.692	Remote Similarity	NPC318020
0.692	Remote Similarity	NPC295228
0.6917	Remote Similarity	NPC476114
0.6911	Remote Similarity	NPC244536
0.6911	Remote Similarity	NPC326930
0.6911	Remote Similarity	NPC475301
0.6911	Remote Similarity	NPC476492
0.6908	Remote Similarity	NPC329631
0.6908	Remote Similarity	NPC220852
0.6906	Remote Similarity	NPC478009
0.6906	Remote Similarity	NPC478010
0.6906	Remote Similarity	NPC322043
0.6906	Remote Similarity	NPC327373
0.6904	Remote Similarity	NPC234078
0.6904	Remote Similarity	NPC271215
0.6904	Remote Similarity	NPC149471
0.6904	Remote Similarity	NPC221100
0.6903	Remote Similarity	NPC182814
0.6901	Remote Similarity	NPC17565
0.6901	Remote Similarity	NPC52254
0.6898	Remote Similarity	NPC21638
0.6897	Remote Similarity	NPC79223
0.6895	Remote Similarity	NPC201508
0.6895	Remote Similarity	NPC160666
0.6892	Remote Similarity	NPC285343
0.689	Remote Similarity	NPC208364

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 NPC472434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	576
0.2-0.3	1039
0.3-0.4	1857
0.4-0.5	2774
0.5-0.6	1867
0.6-0.7	685
0.7-0.8	57
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
0.7735	Intermediate Similarity	NPD5640	Discontinued
0.766	Intermediate Similarity	NPD7426	Phase 1
0.7658	Intermediate Similarity	NPD8421	Discontinued
0.7621	Intermediate Similarity	NPD8370	Discontinued
0.7563	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4372	Phase 1
0.75	Intermediate Similarity	NPD6569	Phase 2
0.7479	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7558	Phase 2
0.7445	Intermediate Similarity	NPD4033	Approved
0.7445	Intermediate Similarity	NPD4035	Approved
0.7445	Intermediate Similarity	NPD4122	Approved
0.7445	Intermediate Similarity	NPD4038	Approved
0.7445	Intermediate Similarity	NPD32	Approved
0.7445	Intermediate Similarity	NPD4039	Approved
0.7445	Intermediate Similarity	NPD31	Approved
0.7445	Intermediate Similarity	NPD4036	Approved
0.7445	Intermediate Similarity	NPD4037	Approved
0.7445	Intermediate Similarity	NPD4034	Approved
0.743	Intermediate Similarity	NPD5482	Discontinued
0.7399	Intermediate Similarity	NPD3477	Phase 2
0.7399	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7359	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD6961	Discontinued
0.7317	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8246	Approved
0.7312	Intermediate Similarity	NPD8247	Approved
0.7308	Intermediate Similarity	NPD4897	Phase 2
0.73	Intermediate Similarity	NPD8479	Phase 2
0.7292	Intermediate Similarity	NPD7675	Phase 3
0.7292	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7674	Phase 3
0.7288	Intermediate Similarity	NPD5948	Phase 2
0.7284	Intermediate Similarity	NPD7796	Approved
0.7284	Intermediate Similarity	NPD7797	Approved
0.7269	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6298	Discontinued
0.7253	Intermediate Similarity	NPD5066	Phase 2
0.7253	Intermediate Similarity	NPD5067	Phase 2
0.7246	Intermediate Similarity	NPD4989	Phase 2
0.724	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD1034	Phase 3
0.7222	Intermediate Similarity	NPD3816	Phase 1
0.7222	Intermediate Similarity	NPD3815	Phase 1
0.7202	Intermediate Similarity	NPD5022	Discontinued
0.7197	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6716	Phase 1
0.7177	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1856	Discontinued
0.716	Intermediate Similarity	NPD5559	Phase 2
0.7155	Intermediate Similarity	NPD1392	Approved
0.7155	Intermediate Similarity	NPD7222	Phase 2
0.7154	Intermediate Similarity	NPD5450	Discontinued
0.7131	Intermediate Similarity	NPD5612	Discontinued
0.7126	Intermediate Similarity	NPD3006	Discontinued
0.7125	Intermediate Similarity	NPD5507	Approved
0.7125	Intermediate Similarity	NPD5506	Approved
0.7119	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6494	Phase 2
0.7113	Intermediate Similarity	NPD7194	Discontinued
0.7112	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8325	Phase 3
0.7101	Intermediate Similarity	NPD8326	Phase 3
0.7098	Intermediate Similarity	NPD7859	Phase 2
0.7097	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8356	Approved
0.7093	Intermediate Similarity	NPD6550	Discontinued
0.7091	Intermediate Similarity	NPD4203	Approved
0.7091	Intermediate Similarity	NPD4204	Approved
0.7089	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7069	Discontinued
0.7071	Intermediate Similarity	NPD6568	Discontinued
0.7063	Intermediate Similarity	NPD7967	Discontinued
0.7051	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8430	Approved
0.7043	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5908	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3003	Approved
0.7036	Intermediate Similarity	NPD8468	Phase 2
0.7036	Intermediate Similarity	NPD8359	Phase 2
0.7034	Intermediate Similarity	NPD4131	Phase 3
0.7026	Intermediate Similarity	NPD7416	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3343	Phase 3
0.7022	Intermediate Similarity	NPD3321	Discontinued
0.702	Intermediate Similarity	NPD8101	Phase 3
0.7017	Intermediate Similarity	NPD5902	Approved
0.7017	Intermediate Similarity	NPD5903	Approved
0.7016	Intermediate Similarity	NPD8049	Phase 2
0.7012	Intermediate Similarity	NPD7417	Discontinued
0.6988	Remote Similarity	NPD4454	Phase 2
0.6984	Remote Similarity	NPD8116	Phase 3
0.6984	Remote Similarity	NPD8117	Approved
0.6983	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8324	Phase 2
0.6977	Remote Similarity	NPD8442	Discontinued
0.6976	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6536	Approved
0.6972	Remote Similarity	NPD6537	Approved
0.6971	Remote Similarity	NPD3763	Approved
0.6971	Remote Similarity	NPD3402	Phase 1
0.6966	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3939	Suspended
0.6953	Remote Similarity	NPD6669	Phase 2
0.6948	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5512	Phase 3
0.6939	Remote Similarity	NPD7603	Discontinued
0.6938	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7452	Approved
0.6936	Remote Similarity	NPD7453	Approved
0.6935	Remote Similarity	NPD6530	Approved
0.6935	Remote Similarity	NPD6531	Approved
0.6935	Remote Similarity	NPD4885	Approved
0.6929	Remote Similarity	NPD6985	Discontinued
0.6923	Remote Similarity	NPD8512	Phase 3
0.692	Remote Similarity	NPD7853	Phase 2
0.692	Remote Similarity	NPD4889	Approved
0.692	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6517	Phase 3
0.6913	Remote Similarity	NPD6206	Phase 1
0.6911	Remote Similarity	NPD4086	Phase 1
0.6908	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7467	Discontinued
0.6902	Remote Similarity	NPD8100	Phase 3
0.6901	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3875	Discontinued
0.69	Remote Similarity	NPD3396	Approved
0.69	Remote Similarity	NPD3395	Approved
0.6894	Remote Similarity	NPD5601	Phase 2
0.6891	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8255	Phase 2
0.6883	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6964	Approved
0.688	Remote Similarity	NPD6963	Approved
0.6875	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6873	Remote Similarity	NPD7405	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5850	Phase 3
0.6872	Remote Similarity	NPD8063	Discontinued
0.687	Remote Similarity	NPD8289	Discontinued
0.687	Remote Similarity	NPD5116	Phase 1
0.6866	Remote Similarity	NPD5018	Phase 3
0.686	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7395	Discontinued
0.6858	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6456	Discontinued
0.6853	Remote Similarity	NPD1768	Approved
0.6848	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD4923	Phase 1
0.6842	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4373	Phase 2
0.6833	Remote Similarity	NPD5944	Phase 1
0.6833	Remote Similarity	NPD5945	Phase 1
0.6831	Remote Similarity	NPD6500	Approved
0.6831	Remote Similarity	NPD6501	Approved
0.6827	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4418	Discontinued
0.6826	Remote Similarity	NPD6590	Discontinued
0.6822	Remote Similarity	NPD7001	Phase 3
0.682	Remote Similarity	NPD5416	Discontinued
0.682	Remote Similarity	NPD3570	Phase 2
0.6809	Remote Similarity	NPD5487	Phase 1
0.6809	Remote Similarity	NPD6276	Discontinued
0.6809	Remote Similarity	NPD5513	Phase 2
0.6808	Remote Similarity	NPD8463	Approved
0.6808	Remote Similarity	NPD7963	Phase 3
0.6805	Remote Similarity	NPD5293	Phase 2
0.68	Remote Similarity	NPD7031	Phase 1
0.6798	Remote Similarity	NPD6750	Phase 2
0.6798	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6281	Approved
0.6792	Remote Similarity	NPD5866	Approved
0.679	Remote Similarity	NPD5632	Approved
0.679	Remote Similarity	NPD4429	Discontinued
0.6789	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7567	Approved
0.6786	Remote Similarity	NPD3386	Phase 2
0.6783	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3825	Phase 3
0.678	Remote Similarity	NPD4795	Phase 2
0.678	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6643	Discontinued
0.6772	Remote Similarity	NPD7886	Phase 2
0.6772	Remote Similarity	NPD7885	Phase 2
0.6772	Remote Similarity	NPD4858	Phase 2
0.677	Remote Similarity	NPD8375	Approved
0.6767	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6988	Phase 1
0.6766	Remote Similarity	NPD5922	Phase 3
0.6763	Remote Similarity	NPD2314	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data