NPASS Compound

Structure

NPC284348 OpenBabel07101718222D 22 22 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 19 2 0 0 0 0 17 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.21
Volume:	338.149
LogP:	2.382
LogD:	2.459
LogS:	-2.266
# Rotatable Bonds:	12
TPSA:	70.42
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	2.389
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.741
MDCK Permeability:	1.9565010006772354e-05
Pgp-inhibitor:	0.559
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.387
Plasma Protein Binding (PPB):	60.93749237060547%
Volume Distribution (VD):	0.917
Pgp-substrate:	19.079164505004883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.244
CYP1A2-substrate:	0.806
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.554
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.683
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	9.717
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.146
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.201
Skin Sensitization:	0.657
Carcinogencity:	0.123
Eye Corrosion:	0.005
Eye Irritation:	0.157
Respiratory Toxicity:	0.776

Download Data

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

Natural Product: NPC284348

Natural Product ID:	NPC284348
*Common Name:**	12'-Hydroxy-7'-Multijuguinone
IUPAC Name:	1-hydroxy-12-(5-hydroxy-6-methylpyridin-2-yl)dodecan-6-one
Synonyms:
Standard InCHIKey:	YRVGMUCBUGPWMR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H29NO3/c1-15-18(22)13-12-16(19-15)9-5-2-3-6-10-17(21)11-7-4-8-14-20/h12-13,20,22H,2-11,14H2,1H3
SMILES:	OCCCCCC(=O)CCCCCCc1ccc(c(n1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087643
PubChem CID:	45378270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0004152] Methylpyridines

*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
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20000694]
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22304303]
NPO9634	Senna multijuga	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	INH	=	0.18	ug	PMID[513239]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	30.0	%	PMID[513239]

☑ 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 NPC284348 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	232
0.1-0.2	2525
0.2-0.3	13504
0.3-0.4	9793
0.4-0.5	12425
0.5-0.6	3328
0.6-0.7	798
0.7-0.8	83
0.8-0.85	2
0.85-0.9	0
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC257142
0.9366	High Similarity	NPC470403
0.9366	High Similarity	NPC470404
0.9366	High Similarity	NPC470394
0.9236	High Similarity	NPC470395
0.9067	High Similarity	NPC116573
0.817	Intermediate Similarity	NPC220523
0.8077	Intermediate Similarity	NPC153769
0.7935	Intermediate Similarity	NPC161292
0.7866	Intermediate Similarity	NPC44161
0.7665	Intermediate Similarity	NPC253810
0.7662	Intermediate Similarity	NPC85443
0.7627	Intermediate Similarity	NPC230403
0.758	Intermediate Similarity	NPC471598
0.7572	Intermediate Similarity	NPC320394
0.755	Intermediate Similarity	NPC174421
0.75	Intermediate Similarity	NPC478032
0.7458	Intermediate Similarity	NPC144381
0.7436	Intermediate Similarity	NPC280853
0.7423	Intermediate Similarity	NPC63562
0.741	Intermediate Similarity	NPC79911
0.7394	Intermediate Similarity	NPC84508
0.7389	Intermediate Similarity	NPC245657
0.7389	Intermediate Similarity	NPC285016
0.7389	Intermediate Similarity	NPC318935
0.7372	Intermediate Similarity	NPC471596
0.7363	Intermediate Similarity	NPC472284
0.7349	Intermediate Similarity	NPC25899
0.7349	Intermediate Similarity	NPC120798
0.7342	Intermediate Similarity	NPC60553
0.7333	Intermediate Similarity	NPC132680
0.7333	Intermediate Similarity	NPC269919
0.733	Intermediate Similarity	NPC241025
0.7294	Intermediate Similarity	NPC314940
0.7294	Intermediate Similarity	NPC473764
0.7288	Intermediate Similarity	NPC194040
0.7267	Intermediate Similarity	NPC303225
0.7263	Intermediate Similarity	NPC3715
0.7257	Intermediate Similarity	NPC219963
0.7246	Intermediate Similarity	NPC324203
0.7246	Intermediate Similarity	NPC322976
0.7246	Intermediate Similarity	NPC63338
0.7244	Intermediate Similarity	NPC328029
0.7225	Intermediate Similarity	NPC194724
0.7216	Intermediate Similarity	NPC314270
0.7207	Intermediate Similarity	NPC183805
0.7202	Intermediate Similarity	NPC48192
0.72	Intermediate Similarity	NPC52831
0.72	Intermediate Similarity	NPC325705
0.7193	Intermediate Similarity	NPC126481
0.7191	Intermediate Similarity	NPC314573
0.7181	Intermediate Similarity	NPC472286
0.7181	Intermediate Similarity	NPC472287
0.7179	Intermediate Similarity	NPC313804
0.7179	Intermediate Similarity	NPC315804
0.7176	Intermediate Similarity	NPC41717
0.7166	Intermediate Similarity	NPC317572
0.716	Intermediate Similarity	NPC263439
0.716	Intermediate Similarity	NPC118511
0.7152	Intermediate Similarity	NPC471594
0.7151	Intermediate Similarity	NPC252590
0.7143	Intermediate Similarity	NPC316403
0.7143	Intermediate Similarity	NPC322644
0.7135	Intermediate Similarity	NPC42591
0.7111	Intermediate Similarity	NPC110741
0.7086	Intermediate Similarity	NPC283152
0.7069	Intermediate Similarity	NPC95898
0.7062	Intermediate Similarity	NPC161887
0.7062	Intermediate Similarity	NPC266551
0.7059	Intermediate Similarity	NPC211187
0.7056	Intermediate Similarity	NPC206186
0.7055	Intermediate Similarity	NPC302159
0.7049	Intermediate Similarity	NPC45850
0.7049	Intermediate Similarity	NPC226202
0.7048	Intermediate Similarity	NPC36168
0.7048	Intermediate Similarity	NPC26872
0.7039	Intermediate Similarity	NPC295158
0.7	Intermediate Similarity	NPC47298
0.7	Intermediate Similarity	NPC315214
0.6983	Remote Similarity	NPC207851
0.6963	Remote Similarity	NPC283117
0.6963	Remote Similarity	NPC53344
0.6959	Remote Similarity	NPC32028
0.6959	Remote Similarity	NPC159319
0.6952	Remote Similarity	NPC280714
0.6948	Remote Similarity	NPC278451
0.6947	Remote Similarity	NPC472259
0.6931	Remote Similarity	NPC186351
0.6928	Remote Similarity	NPC151489
0.6923	Remote Similarity	NPC26850
0.6919	Remote Similarity	NPC471178
0.6907	Remote Similarity	NPC294375
0.6906	Remote Similarity	NPC90415
0.6904	Remote Similarity	NPC293151
0.6901	Remote Similarity	NPC59779
0.6901	Remote Similarity	NPC177404
0.6901	Remote Similarity	NPC124542
0.6901	Remote Similarity	NPC471177
0.69	Remote Similarity	NPC478141
0.6897	Remote Similarity	NPC256828
0.6895	Remote Similarity	NPC476098
0.6868	Remote Similarity	NPC36498
0.6867	Remote Similarity	NPC13432
0.686	Remote Similarity	NPC473057
0.6857	Remote Similarity	NPC158129
0.6851	Remote Similarity	NPC20249
0.6848	Remote Similarity	NPC114974
0.6847	Remote Similarity	NPC244536
0.6839	Remote Similarity	NPC470894
0.6837	Remote Similarity	NPC250448
0.6828	Remote Similarity	NPC276517
0.6818	Remote Similarity	NPC471294
0.6818	Remote Similarity	NPC259545
0.6796	Remote Similarity	NPC62069
0.6782	Remote Similarity	NPC108469
0.6778	Remote Similarity	NPC118776
0.6772	Remote Similarity	NPC18487
0.6761	Remote Similarity	NPC121658
0.6761	Remote Similarity	NPC14651
0.676	Remote Similarity	NPC472168
0.6755	Remote Similarity	NPC90229
0.6743	Remote Similarity	NPC1527
0.6742	Remote Similarity	NPC286195
0.6742	Remote Similarity	NPC84347
0.6742	Remote Similarity	NPC288943
0.674	Remote Similarity	NPC243058
0.6739	Remote Similarity	NPC230805
0.672	Remote Similarity	NPC306376
0.6717	Remote Similarity	NPC118228
0.6705	Remote Similarity	NPC476518
0.6703	Remote Similarity	NPC203635
0.6701	Remote Similarity	NPC321428
0.669	Remote Similarity	NPC255721
0.6685	Remote Similarity	NPC66083
0.6685	Remote Similarity	NPC312872
0.6667	Remote Similarity	NPC477889
0.6667	Remote Similarity	NPC232340
0.6667	Remote Similarity	NPC477111
0.665	Remote Similarity	NPC9894
0.6649	Remote Similarity	NPC315491
0.6649	Remote Similarity	NPC249040
0.6649	Remote Similarity	NPC45459
0.6648	Remote Similarity	NPC150048
0.6648	Remote Similarity	NPC203754
0.6631	Remote Similarity	NPC471448
0.663	Remote Similarity	NPC249662
0.663	Remote Similarity	NPC478023
0.6629	Remote Similarity	NPC474409
0.6626	Remote Similarity	NPC47986
0.6618	Remote Similarity	NPC51388
0.6617	Remote Similarity	NPC174576
0.6616	Remote Similarity	NPC12344
0.6615	Remote Similarity	NPC88008
0.6615	Remote Similarity	NPC193238
0.66	Remote Similarity	NPC469928
0.6598	Remote Similarity	NPC329708
0.6598	Remote Similarity	NPC118832
0.6598	Remote Similarity	NPC47059
0.6598	Remote Similarity	NPC165349
0.6598	Remote Similarity	NPC137929
0.6598	Remote Similarity	NPC264166
0.6598	Remote Similarity	NPC274291
0.6598	Remote Similarity	NPC164374
0.6597	Remote Similarity	NPC476167
0.6597	Remote Similarity	NPC128823
0.6595	Remote Similarity	NPC238242
0.6587	Remote Similarity	NPC477112
0.6583	Remote Similarity	NPC232225
0.6579	Remote Similarity	NPC473814
0.6579	Remote Similarity	NPC78767
0.6575	Remote Similarity	NPC88363
0.6575	Remote Similarity	NPC67659
0.6566	Remote Similarity	NPC23294
0.6564	Remote Similarity	NPC471736
0.6562	Remote Similarity	NPC213308
0.6561	Remote Similarity	NPC93390
0.6557	Remote Similarity	NPC133306
0.6556	Remote Similarity	NPC134586
0.6555	Remote Similarity	NPC477516
0.6552	Remote Similarity	NPC285635
0.6552	Remote Similarity	NPC76327
0.6546	Remote Similarity	NPC134848
0.6545	Remote Similarity	NPC192315
0.6543	Remote Similarity	NPC114335
0.6543	Remote Similarity	NPC141915
0.6543	Remote Similarity	NPC56170
0.6543	Remote Similarity	NPC280964
0.6538	Remote Similarity	NPC271792
0.6538	Remote Similarity	NPC15840
0.6537	Remote Similarity	NPC205372
0.6536	Remote Similarity	NPC111624
0.6533	Remote Similarity	NPC219087
0.6531	Remote Similarity	NPC270918
0.6526	Remote Similarity	NPC109922
0.6525	Remote Similarity	NPC213774
0.6519	Remote Similarity	NPC219848
0.6519	Remote Similarity	NPC211997
0.6517	Remote Similarity	NPC477110
0.6517	Remote Similarity	NPC330009
0.6517	Remote Similarity	NPC74969

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 NPC284348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	635
0.2-0.3	948
0.3-0.4	1371
0.4-0.5	3600
0.5-0.6	2071
0.6-0.7	321
0.7-0.8	23
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8354	Intermediate Similarity	NPD861	Approved
0.8354	Intermediate Similarity	NPD863	Approved
0.8354	Intermediate Similarity	NPD862	Approved
0.805	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6159	Phase 2
0.7516	Intermediate Similarity	NPD3525	Discontinued
0.7368	Intermediate Similarity	NPD158	Discontinued
0.7333	Intermediate Similarity	NPD9382	Approved
0.7333	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9383	Approved
0.7273	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5316	Approved
0.7253	Intermediate Similarity	NPD5512	Phase 3
0.7246	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD2177	Approved
0.7228	Intermediate Similarity	NPD2175	Phase 3
0.7228	Intermediate Similarity	NPD2176	Approved
0.72	Intermediate Similarity	NPD9510	Approved
0.7195	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8356	Approved
0.7069	Intermediate Similarity	NPD9690	Approved
0.7056	Intermediate Similarity	NPD2383	Phase 1
0.7052	Intermediate Similarity	NPD2123	Phase 3
0.7019	Intermediate Similarity	NPD4805	Approved
0.7	Intermediate Similarity	NPD1684	Approved
0.7	Intermediate Similarity	NPD1685	Approved
0.6982	Remote Similarity	NPD5255	Approved
0.6977	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5429	Discontinued
0.6941	Remote Similarity	NPD112	Approved
0.6941	Remote Similarity	NPD9705	Discontinued
0.6939	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD8430	Approved
0.6907	Remote Similarity	NPD5416	Discontinued
0.6907	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD565	Phase 2
0.6894	Remote Similarity	NPD4804	Approved
0.6885	Remote Similarity	NPD1213	Phase 3
0.6875	Remote Similarity	NPD6290	Phase 2
0.6872	Remote Similarity	NPD4203	Approved
0.6872	Remote Similarity	NPD4204	Approved
0.6868	Remote Similarity	NPD9363	Approved
0.6868	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD9364	Phase 2
0.686	Remote Similarity	NPD5088	Discontinued
0.6847	Remote Similarity	NPD4086	Phase 1
0.6839	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD852	Discontinued
0.6821	Remote Similarity	NPD5936	Approved
0.6821	Remote Similarity	NPD5939	Approved
0.6821	Remote Similarity	NPD4502	Phase 2
0.6802	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6641	Approved
0.6798	Remote Similarity	NPD6642	Approved
0.6786	Remote Similarity	NPD6158	Phase 2
0.6786	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9695	Approved
0.676	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD180	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD408	Approved
0.6739	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6590	Discontinued
0.6725	Remote Similarity	NPD2582	Approved
0.6725	Remote Similarity	NPD2581	Approved
0.6717	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3321	Discontinued
0.6702	Remote Similarity	NPD6550	Discontinued
0.6686	Remote Similarity	NPD9595	Approved
0.6686	Remote Similarity	NPD2882	Phase 1
0.6686	Remote Similarity	NPD9596	Approved
0.6685	Remote Similarity	NPD1034	Phase 3
0.6685	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2916	Discontinued
0.6667	Remote Similarity	NPD1229	Phase 2
0.6667	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3920	Phase 2
0.6667	Remote Similarity	NPD6988	Phase 1
0.6667	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5003	Discontinued
0.6649	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD484	Approved
0.6648	Remote Similarity	NPD2380	Approved
0.6648	Remote Similarity	NPD2781	Approved
0.6648	Remote Similarity	NPD2844	Phase 3
0.6648	Remote Similarity	NPD2381	Approved
0.6648	Remote Similarity	NPD2382	Approved
0.6647	Remote Similarity	NPD2511	Approved
0.6634	Remote Similarity	NPD7603	Discontinued
0.6631	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD6569	Phase 2
0.663	Remote Similarity	NPD5256	Discontinued
0.663	Remote Similarity	NPD3315	Phase 3
0.6629	Remote Similarity	NPD2780	Approved
0.6629	Remote Similarity	NPD43	Approved
0.6629	Remote Similarity	NPD6182	Approved
0.6629	Remote Similarity	NPD2782	Approved
0.6629	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD926	Approved
0.6629	Remote Similarity	NPD925	Approved
0.6617	Remote Similarity	NPD7395	Discontinued
0.6614	Remote Similarity	NPD3477	Phase 2
0.6614	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2565	Phase 2
0.6613	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2564	Approved
0.661	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5420	Discontinued
0.6598	Remote Similarity	NPD4035	Approved
0.6598	Remote Similarity	NPD32	Approved
0.6598	Remote Similarity	NPD4122	Approved
0.6598	Remote Similarity	NPD4038	Approved
0.6598	Remote Similarity	NPD4037	Approved
0.6598	Remote Similarity	NPD4034	Approved
0.6598	Remote Similarity	NPD4039	Approved
0.6598	Remote Similarity	NPD31	Approved
0.6598	Remote Similarity	NPD4036	Approved
0.6598	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4033	Approved
0.6593	Remote Similarity	NPD9362	Approved
0.6592	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD424	Approved
0.6591	Remote Similarity	NPD425	Approved
0.658	Remote Similarity	NPD2779	Approved
0.6575	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3717	Discontinued
0.6562	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3395	Approved
0.6561	Remote Similarity	NPD3396	Approved
0.6561	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5596	Phase 2
0.6553	Remote Similarity	NPD5640	Discontinued
0.6553	Remote Similarity	NPD3263	Phase 3
0.6552	Remote Similarity	NPD9507	Approved
0.655	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2727	Phase 2
0.6545	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD772	Phase 3
0.6545	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD9689	Approved
0.6538	Remote Similarity	NPD5022	Discontinued
0.6535	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4429	Discontinued
0.6533	Remote Similarity	NPD7069	Discontinued
0.6532	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7222	Phase 2
0.6524	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2896	Discontinued
0.6522	Remote Similarity	NPD1096	Discontinued
0.652	Remote Similarity	NPD7726	Phase 1
0.6517	Remote Similarity	NPD5319	Approved
0.6517	Remote Similarity	NPD5320	Approved
0.6508	Remote Similarity	NPD4526	Approved
0.6508	Remote Similarity	NPD4529	Approved
0.6508	Remote Similarity	NPD4528	Approved
0.6506	Remote Similarity	NPD1592	Phase 3
0.6503	Remote Similarity	NPD3178	Discontinued
0.6503	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6974	Phase 3
0.65	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4889	Approved
0.6485	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1631	Approved
0.6477	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD4897	Phase 2
0.6462	Remote Similarity	NPD5513	Phase 2
0.6458	Remote Similarity	NPD7778	Approved
0.6458	Remote Similarity	NPD7777	Approved
0.6458	Remote Similarity	NPD53	Approved
0.6456	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.645	Remote Similarity	NPD5866	Approved
0.6432	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD3392	Approved
0.6425	Remote Similarity	NPD2778	Approved
0.6424	Remote Similarity	NPD9342	Approved
0.6422	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD9376	Approved
0.6418	Remote Similarity	NPD3945	Discontinued
0.6415	Remote Similarity	NPD3074	Discontinued
0.6414	Remote Similarity	NPD6376	Discontinued
0.6413	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4703	Approved
0.6412	Remote Similarity	NPD4702	Approved
0.641	Remote Similarity	NPD522	Approved
0.6407	Remote Similarity	NPD5020	Approved
0.6406	Remote Similarity	NPD2952	Discontinued
0.64	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2762	Phase 2
0.6381	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8405	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