NPASS Compound

Structure

NPC49184 OpenBabel07101718202D 26 30 0 0 1 0 0 0 0 0999 V2000 -4.6665 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5339 -3.0291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5686 -3.2905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7900 -2.0624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2133 0.3695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8596 -2.5853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0810 -1.3573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5047 0.4233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6190 -0.2254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1158 -1.6187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 -3.0827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -0.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -1.0827 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 1 13 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 22 1 0 0 0 0 13 21 2 0 0 0 0 13 23 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 9 1 6 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 24 2 0 0 0 0 21 25 1 0 0 0 0 22 14 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	347.15
Volume:	362.562
LogP:	4.015
LogD:	3.002
LogS:	-4.692
# Rotatable Bonds:	2
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	4.384
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	1.3348163520277012e-05
Pgp-inhibitor:	0.108
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	92.8244857788086%
Volume Distribution (VD):	0.762
Pgp-substrate:	3.1402275562286377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.451
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.803
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.614
CYP2D6-substrate:	0.745
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.925

ADMET: Excretion

Clearance (CL):	1.956
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.448
Human Hepatotoxicity (H-HT):	0.515
Drug-inuced Liver Injury (DILI):	0.506
AMES Toxicity:	0.709
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.864
Carcinogencity:	0.819
Eye Corrosion:	0.004
Eye Irritation:	0.154
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC49184

Natural Product ID:	NPC49184
*Common Name:**	PKYCMYNWURXMPV-JTSKRJEESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PKYCMYNWURXMPV-JTSKRJEESA-N
Standard InCHI:	InChI=1S/C22H21NO3/c1-13-21(25-2)20(24)19-16(23-13)11-10-15-18(19)17-9-6-12-22(15,26-17)14-7-4-3-5-8-14/h3-5,7-8,10-11,17H,6,9,12H2,1-2H3,(H,23,24)/t17-,22-/m0/s1
SMILES:	Cc1c(c(=O)c2c(ccc3c2[C@@H]2CCC[C@@]3(c3ccccc3)O2)[nH]1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105822
PubChem CID:	76317432
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO32614	melochia odorata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24392742]

☑ 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
EC50	1
Others	3

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		TI	=	13.0	n.a.	PMID[506144]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	>	50.0	%	PMID[506144]
NPT27	Others	Unspecified		LC50	=	11000.0	nM	PMID[506144]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	840.0	nM	PMID[506144]

☑ 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 NPC49184 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	544
0.1-0.2	2783
0.2-0.3	11365
0.3-0.4	7262
0.4-0.5	15262
0.5-0.6	3560
0.6-0.7	1623
0.7-0.8	279
0.8-0.85	9
0.85-0.9	5
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8817	High Similarity	NPC25961
0.776	Intermediate Similarity	NPC472163
0.7526	Intermediate Similarity	NPC241263
0.7513	Intermediate Similarity	NPC477998
0.7424	Intermediate Similarity	NPC313112
0.7424	Intermediate Similarity	NPC301292
0.7356	Intermediate Similarity	NPC242000
0.7337	Intermediate Similarity	NPC307640
0.7312	Intermediate Similarity	NPC186669
0.7264	Intermediate Similarity	NPC222561
0.7236	Intermediate Similarity	NPC288759
0.7211	Intermediate Similarity	NPC97584
0.7208	Intermediate Similarity	NPC234933
0.7188	Intermediate Similarity	NPC14994
0.7182	Intermediate Similarity	NPC93653
0.7178	Intermediate Similarity	NPC478075
0.7178	Intermediate Similarity	NPC198160
0.7168	Intermediate Similarity	NPC308197
0.7166	Intermediate Similarity	NPC264482
0.7166	Intermediate Similarity	NPC203202
0.7165	Intermediate Similarity	NPC25401
0.7158	Intermediate Similarity	NPC299582
0.7143	Intermediate Similarity	NPC283810
0.7087	Intermediate Similarity	NPC116178
0.7077	Intermediate Similarity	NPC1820
0.7068	Intermediate Similarity	NPC159963
0.7056	Intermediate Similarity	NPC21483
0.7056	Intermediate Similarity	NPC198205
0.7053	Intermediate Similarity	NPC321166
0.7053	Intermediate Similarity	NPC217903
0.7035	Intermediate Similarity	NPC112752
0.7035	Intermediate Similarity	NPC311054
0.7019	Intermediate Similarity	NPC176113
0.7019	Intermediate Similarity	NPC298449
0.6985	Remote Similarity	NPC198390
0.698	Remote Similarity	NPC15987
0.6979	Remote Similarity	NPC470317
0.6957	Remote Similarity	NPC293458
0.6931	Remote Similarity	NPC136573
0.6931	Remote Similarity	NPC176371
0.6927	Remote Similarity	NPC477999
0.6927	Remote Similarity	NPC308943
0.6923	Remote Similarity	NPC151171
0.6915	Remote Similarity	NPC107828
0.6915	Remote Similarity	NPC90358
0.6912	Remote Similarity	NPC87714
0.6911	Remote Similarity	NPC218594
0.6911	Remote Similarity	NPC99043
0.6911	Remote Similarity	NPC6974
0.6908	Remote Similarity	NPC474366
0.6897	Remote Similarity	NPC475223
0.6895	Remote Similarity	NPC129624
0.6875	Remote Similarity	NPC85613
0.6875	Remote Similarity	NPC5167
0.6875	Remote Similarity	NPC218303
0.6863	Remote Similarity	NPC246983
0.6863	Remote Similarity	NPC475448
0.6862	Remote Similarity	NPC469915
0.686	Remote Similarity	NPC173295
0.6857	Remote Similarity	NPC55470
0.684	Remote Similarity	NPC77777
0.6829	Remote Similarity	NPC268077
0.6829	Remote Similarity	NPC133156
0.6822	Remote Similarity	NPC329830
0.6822	Remote Similarity	NPC280799
0.6812	Remote Similarity	NPC207873
0.6812	Remote Similarity	NPC100573
0.6812	Remote Similarity	NPC90185
0.6809	Remote Similarity	NPC224970
0.6809	Remote Similarity	NPC470971
0.6809	Remote Similarity	NPC223595
0.6809	Remote Similarity	NPC167724
0.6805	Remote Similarity	NPC122235
0.6804	Remote Similarity	NPC474688
0.6793	Remote Similarity	NPC123241
0.6789	Remote Similarity	NPC177261
0.6782	Remote Similarity	NPC71124
0.678	Remote Similarity	NPC207971
0.6768	Remote Similarity	NPC45389
0.6768	Remote Similarity	NPC313293
0.675	Remote Similarity	NPC254957
0.6749	Remote Similarity	NPC5374
0.674	Remote Similarity	NPC144691
0.6736	Remote Similarity	NPC321211
0.6735	Remote Similarity	NPC322621
0.6734	Remote Similarity	NPC22476
0.673	Remote Similarity	NPC30749
0.6728	Remote Similarity	NPC115588
0.6727	Remote Similarity	NPC179605
0.6727	Remote Similarity	NPC279385
0.672	Remote Similarity	NPC248117
0.6719	Remote Similarity	NPC471743
0.6719	Remote Similarity	NPC84347
0.6715	Remote Similarity	NPC477161
0.6703	Remote Similarity	NPC61013
0.6702	Remote Similarity	NPC96901
0.6701	Remote Similarity	NPC160381
0.67	Remote Similarity	NPC206109
0.67	Remote Similarity	NPC193906
0.67	Remote Similarity	NPC23080
0.67	Remote Similarity	NPC114039
0.6699	Remote Similarity	NPC41216
0.6687	Remote Similarity	NPC103292
0.6685	Remote Similarity	NPC237649
0.6685	Remote Similarity	NPC114808
0.6685	Remote Similarity	NPC300596
0.6684	Remote Similarity	NPC471742
0.6683	Remote Similarity	NPC474059
0.6683	Remote Similarity	NPC5630
0.6682	Remote Similarity	NPC154922
0.6682	Remote Similarity	NPC305542
0.6667	Remote Similarity	NPC193410
0.6667	Remote Similarity	NPC279527
0.6667	Remote Similarity	NPC214960
0.6667	Remote Similarity	NPC471652
0.6667	Remote Similarity	NPC470579
0.6652	Remote Similarity	NPC474701
0.6647	Remote Similarity	NPC268534
0.6637	Remote Similarity	NPC475844
0.6636	Remote Similarity	NPC473837
0.6636	Remote Similarity	NPC251071
0.6635	Remote Similarity	NPC61731
0.6635	Remote Similarity	NPC186569
0.6623	Remote Similarity	NPC67401
0.6618	Remote Similarity	NPC100863
0.6603	Remote Similarity	NPC212123
0.6602	Remote Similarity	NPC232600
0.6601	Remote Similarity	NPC303214
0.6597	Remote Similarity	NPC472118
0.6596	Remote Similarity	NPC176983
0.6584	Remote Similarity	NPC471825
0.6583	Remote Similarity	NPC181928
0.6583	Remote Similarity	NPC21425
0.6582	Remote Similarity	NPC190461
0.6579	Remote Similarity	NPC182131
0.6574	Remote Similarity	NPC223590
0.6573	Remote Similarity	NPC124658
0.6573	Remote Similarity	NPC227361
0.6571	Remote Similarity	NPC285192
0.6568	Remote Similarity	NPC226794
0.6567	Remote Similarity	NPC203628
0.6564	Remote Similarity	NPC475094
0.6562	Remote Similarity	NPC471604
0.6559	Remote Similarity	NPC36836
0.6559	Remote Similarity	NPC63370
0.6558	Remote Similarity	NPC471197
0.6555	Remote Similarity	NPC246140
0.6555	Remote Similarity	NPC195787
0.6555	Remote Similarity	NPC45190
0.6552	Remote Similarity	NPC230313
0.6547	Remote Similarity	NPC139373
0.6547	Remote Similarity	NPC49547
0.6545	Remote Similarity	NPC285254
0.6544	Remote Similarity	NPC225279
0.6542	Remote Similarity	NPC189661
0.6537	Remote Similarity	NPC17677
0.6536	Remote Similarity	NPC472241
0.6535	Remote Similarity	NPC113455
0.6535	Remote Similarity	NPC469722
0.6532	Remote Similarity	NPC223242
0.6532	Remote Similarity	NPC231382
0.6528	Remote Similarity	NPC471198
0.6528	Remote Similarity	NPC73280
0.6528	Remote Similarity	NPC298851
0.6528	Remote Similarity	NPC276993
0.6528	Remote Similarity	NPC210415
0.6528	Remote Similarity	NPC191310
0.6528	Remote Similarity	NPC293255
0.6528	Remote Similarity	NPC181138
0.6528	Remote Similarity	NPC21752
0.6517	Remote Similarity	NPC312531
0.6517	Remote Similarity	NPC105055
0.6517	Remote Similarity	NPC22689
0.6517	Remote Similarity	NPC473298
0.6516	Remote Similarity	NPC74575
0.6516	Remote Similarity	NPC13249
0.6514	Remote Similarity	NPC198503
0.6513	Remote Similarity	NPC285941
0.6512	Remote Similarity	NPC209389
0.6509	Remote Similarity	NPC314834
0.6508	Remote Similarity	NPC472121
0.6508	Remote Similarity	NPC99632
0.6508	Remote Similarity	NPC282339
0.6508	Remote Similarity	NPC286871
0.6507	Remote Similarity	NPC38961
0.65	Remote Similarity	NPC473815
0.65	Remote Similarity	NPC122886
0.6498	Remote Similarity	NPC256422
0.6495	Remote Similarity	NPC469726
0.6495	Remote Similarity	NPC329338
0.6495	Remote Similarity	NPC268223
0.649	Remote Similarity	NPC1464
0.6488	Remote Similarity	NPC470021
0.6488	Remote Similarity	NPC257490
0.6484	Remote Similarity	NPC144452
0.6482	Remote Similarity	NPC52262
0.6481	Remote Similarity	NPC195636
0.6479	Remote Similarity	NPC220241
0.6479	Remote Similarity	NPC295479
0.6479	Remote Similarity	NPC9894

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 NPC49184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	680
0.2-0.3	913
0.3-0.4	1749
0.4-0.5	2819
0.5-0.6	1978
0.6-0.7	623
0.7-0.8	44
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
0.7514	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5997	Discontinued
0.7235	Intermediate Similarity	NPD1626	Approved
0.7159	Intermediate Similarity	NPD4888	Discontinued
0.7083	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1625	Approved
0.7059	Intermediate Similarity	NPD4859	Phase 1
0.7043	Intermediate Similarity	NPD5183	Approved
0.7043	Intermediate Similarity	NPD5186	Approved
0.7021	Intermediate Similarity	NPD5466	Approved
0.7017	Intermediate Similarity	NPD2836	Approved
0.7	Intermediate Similarity	NPD5086	Approved
0.6931	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5430	Discontinued
0.6872	Remote Similarity	NPD7528	Approved
0.6859	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3399	Approved
0.6823	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1801	Approved
0.6816	Remote Similarity	NPD1802	Approved
0.6791	Remote Similarity	NPD7035	Approved
0.6791	Remote Similarity	NPD7036	Phase 3
0.6784	Remote Similarity	NPD5937	Approved
0.6782	Remote Similarity	NPD2670	Approved
0.678	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6238	Discontinued
0.6734	Remote Similarity	NPD5504	Discontinued
0.6733	Remote Similarity	NPD5515	Phase 2
0.6718	Remote Similarity	NPD8281	Discontinued
0.6704	Remote Similarity	NPD6185	Discontinued
0.67	Remote Similarity	NPD4668	Phase 2
0.67	Remote Similarity	NPD5197	Approved
0.67	Remote Similarity	NPD5194	Approved
0.67	Remote Similarity	NPD5071	Phase 2
0.67	Remote Similarity	NPD5196	Approved
0.6683	Remote Similarity	NPD5928	Phase 1
0.665	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3776	Discontinued
0.6648	Remote Similarity	NPD3170	Approved
0.6636	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6758	Approved
0.6629	Remote Similarity	NPD1189	Approved
0.6619	Remote Similarity	NPD4506	Discontinued
0.6603	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5411	Discontinued
0.6592	Remote Similarity	NPD7922	Phase 1
0.6588	Remote Similarity	NPD552	Approved
0.6588	Remote Similarity	NPD553	Approved
0.6588	Remote Similarity	NPD9567	Approved
0.6585	Remote Similarity	NPD3297	Approved
0.6575	Remote Similarity	NPD4041	Approved
0.6575	Remote Similarity	NPD4607	Approved
0.6559	Remote Similarity	NPD6571	Approved
0.6559	Remote Similarity	NPD2672	Discontinued
0.6559	Remote Similarity	NPD6570	Approved
0.6556	Remote Similarity	NPD7487	Discontinued
0.6555	Remote Similarity	NPD7010	Phase 3
0.6541	Remote Similarity	NPD2790	Discontinued
0.6538	Remote Similarity	NPD3352	Approved
0.6536	Remote Similarity	NPD2923	Approved
0.6522	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7606	Phase 3
0.6513	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8149	Discontinued
0.6512	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3298	Approved
0.6503	Remote Similarity	NPD4161	Discontinued
0.65	Remote Similarity	NPD6484	Approved
0.65	Remote Similarity	NPD4430	Phase 2
0.65	Remote Similarity	NPD6483	Approved
0.6498	Remote Similarity	NPD6770	Approved
0.6497	Remote Similarity	NPD3470	Approved
0.6497	Remote Similarity	NPD3471	Approved
0.6488	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6995	Phase 1
0.6482	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD8008	Approved
0.6474	Remote Similarity	NPD8007	Approved
0.6473	Remote Similarity	NPD3289	Phase 3
0.6473	Remote Similarity	NPD3290	Approved
0.6468	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4513	Discontinued
0.6465	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD2435	Approved
0.6461	Remote Similarity	NPD1109	Approved
0.6461	Remote Similarity	NPD1110	Approved
0.6459	Remote Similarity	NPD6445	Discontinued
0.6457	Remote Similarity	NPD4981	Phase 2
0.6455	Remote Similarity	NPD7244	Discontinued
0.6453	Remote Similarity	NPD7569	Approved
0.6453	Remote Similarity	NPD7570	Approved
0.6449	Remote Similarity	NPD7225	Discontinued
0.6449	Remote Similarity	NPD7301	Phase 3
0.6448	Remote Similarity	NPD7478	Approved
0.6447	Remote Similarity	NPD4330	Approved
0.6447	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4329	Approved
0.6441	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3964	Approved
0.6432	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5860	Discontinued
0.6429	Remote Similarity	NPD5810	Discontinued
0.6429	Remote Similarity	NPD5498	Phase 2
0.6429	Remote Similarity	NPD3947	Discontinued
0.6429	Remote Similarity	NPD3792	Approved
0.6422	Remote Similarity	NPD5610	Approved
0.642	Remote Similarity	NPD5185	Approved
0.642	Remote Similarity	NPD5184	Approved
0.642	Remote Similarity	NPD5182	Approved
0.6418	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4082	Approved
0.6415	Remote Similarity	NPD5950	Discontinued
0.6411	Remote Similarity	NPD7626	Approved
0.6411	Remote Similarity	NPD7627	Approved
0.641	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7324	Discontinued
0.6409	Remote Similarity	NPD8311	Discontinued
0.6408	Remote Similarity	NPD5003	Discontinued
0.6408	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5195	Discontinued
0.6406	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4493	Discontinued
0.639	Remote Similarity	NPD7256	Discontinued
0.6387	Remote Similarity	NPD1309	Phase 2
0.6387	Remote Similarity	NPD1307	Phase 2
0.6386	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD4952	Phase 3
0.638	Remote Similarity	NPD7279	Phase 2
0.638	Remote Similarity	NPD7278	Phase 2
0.6378	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2387	Approved
0.6374	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5918	Discontinued
0.6373	Remote Similarity	NPD2247	Approved
0.6373	Remote Similarity	NPD2249	Approved
0.6373	Remote Similarity	NPD6457	Approved
0.6372	Remote Similarity	NPD6625	Approved
0.6364	Remote Similarity	NPD6321	Discontinued
0.6364	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7476	Discontinued
0.6364	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD2564	Approved
0.6355	Remote Similarity	NPD2565	Phase 2
0.6351	Remote Similarity	NPD3925	Approved
0.6351	Remote Similarity	NPD6250	Discontinued
0.635	Remote Similarity	NPD2971	Approved
0.635	Remote Similarity	NPD2968	Approved
0.6347	Remote Similarity	NPD5496	Approved
0.6339	Remote Similarity	NPD6017	Discontinued
0.6337	Remote Similarity	NPD1574	Approved
0.6335	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD4871	Phase 2
0.6327	Remote Similarity	NPD7940	Phase 3
0.6326	Remote Similarity	NPD1945	Phase 1
0.6323	Remote Similarity	NPD7186	Phase 3
0.6321	Remote Similarity	NPD6037	Discontinued
0.6319	Remote Similarity	NPD7082	Approved
0.6319	Remote Similarity	NPD2820	Phase 3
0.6316	Remote Similarity	NPD4501	Approved
0.6316	Remote Similarity	NPD4500	Approved
0.6316	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7775	Approved
0.6311	Remote Similarity	NPD6199	Discontinued
0.6303	Remote Similarity	NPD2920	Discontinued
0.6303	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1593	Approved
0.63	Remote Similarity	NPD4373	Phase 2
0.6296	Remote Similarity	NPD1208	Approved
0.6296	Remote Similarity	NPD4494	Approved
0.6296	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4492	Approved
0.6292	Remote Similarity	NPD2331	Discontinued
0.6289	Remote Similarity	NPD2037	Approved
0.6284	Remote Similarity	NPD3393	Approved
0.6284	Remote Similarity	NPD3394	Approved
0.6284	Remote Similarity	NPD3389	Approved
0.6283	Remote Similarity	NPD6962	Phase 2
0.6283	Remote Similarity	NPD7688	Phase 1
0.6283	Remote Similarity	NPD8067	Phase 3
0.6281	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD6644	Discontinued
0.6269	Remote Similarity	NPD7546	Discontinued
0.6269	Remote Similarity	NPD4412	Phase 2
0.6269	Remote Similarity	NPD3436	Approved
0.6268	Remote Similarity	NPD5608	Approved
0.6268	Remote Similarity	NPD5609	Approved
0.6264	Remote Similarity	NPD2365	Approved
0.6262	Remote Similarity	NPD7302	Phase 3
0.6262	Remote Similarity	NPD4022	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