NPASS Compound

Structure

NPC473185 OpenBabel07101718292D 31 36 0 0 0 0 0 0 0 0999 V2000 -5.4467 2.5387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2850 -2.1316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6159 -2.8747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9760 -1.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6377 -2.6668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8069 0.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8506 0.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1377 1.5876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9978 -0.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4978 -0.1066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3287 -1.7158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5197 -0.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1596 1.3797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 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 -4.4152 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4904 2.1229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 31 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 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 18 2 0 0 0 0 8 19 2 0 0 0 0 9 22 2 0 0 0 0 10 23 2 0 0 0 0 11 16 1 0 0 0 0 11 20 2 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 26 2 0 0 0 0 14 24 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 25 2 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 27 1 0 0 0 0 26 31 1 0 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.17
Volume:	432.146
LogP:	6.128
LogD:	4.499
LogS:	-6.848
# Rotatable Bonds:	3
TPSA:	50.18
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	2.409
Fsp3:	0.111
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:	-5.406
MDCK Permeability:	1.3868432688468602e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	98.43802642822266%
Volume Distribution (VD):	0.875
Pgp-substrate:	0.7387558817863464%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.79
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.946
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.323

ADMET: Excretion

Clearance (CL):	7.282
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.899
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.807
Carcinogencity:	0.914
Eye Corrosion:	0.003
Eye Irritation:	0.913
Respiratory Toxicity:	0.782

Download Data

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

Natural Product: NPC473185

Natural Product ID:	NPC473185
*Common Name:**	MJDYWDBSCYNOTB-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MJDYWDBSCYNOTB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H22N2O2/c1-16-11-20-19-8-4-6-10-23(19)29(24(20)14-25(16)30)15-17-12-21-18-7-3-5-9-22(18)28-27(21)26(13-17)31-2/h3-14,28,30H,15H2,1-2H3
SMILES:	COc1cc(cc2c1[nH]c1c2cccc1)Cn1c2ccccc2c2c1cc(O)c(c2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633081
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO33199	murraya tetramera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26327273]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Activity	<	80.0	%	PMID[529049]

☑ 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 NPC473185 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	704
0.1-0.2	4602
0.2-0.3	12640
0.3-0.4	7646
0.4-0.5	12036
0.5-0.6	2947
0.6-0.7	1597
0.7-0.8	446
0.8-0.85	57
0.85-0.9	13
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9652	High Similarity	NPC473179
0.9617	High Similarity	NPC473183
0.9522	High Similarity	NPC473184
0.9412	High Similarity	NPC132642
0.9378	High Similarity	NPC475253
0.9353	High Similarity	NPC94157
0.9108	High Similarity	NPC473182
0.8915	High Similarity	NPC202503
0.8878	High Similarity	NPC199667
0.8829	High Similarity	NPC473181
0.8792	High Similarity	NPC473180
0.8726	High Similarity	NPC477532
0.8679	High Similarity	NPC477533
0.8657	High Similarity	NPC243834
0.8657	High Similarity	NPC70956
0.8657	High Similarity	NPC252251
0.8647	High Similarity	NPC209769
0.8578	High Similarity	NPC477531
0.8551	High Similarity	NPC193777
0.8545	High Similarity	NPC39370
0.8544	High Similarity	NPC470930
0.8539	High Similarity	NPC473186
0.8532	High Similarity	NPC209174
0.848	Intermediate Similarity	NPC128823
0.8447	Intermediate Similarity	NPC475085
0.8447	Intermediate Similarity	NPC475112
0.8447	Intermediate Similarity	NPC291535
0.8406	Intermediate Similarity	NPC475774
0.8374	Intermediate Similarity	NPC131017
0.8349	Intermediate Similarity	NPC48353
0.8318	Intermediate Similarity	NPC170114
0.8317	Intermediate Similarity	NPC162484
0.831	Intermediate Similarity	NPC471080
0.831	Intermediate Similarity	NPC469592
0.8308	Intermediate Similarity	NPC242928
0.8304	Intermediate Similarity	NPC473188
0.8271	Intermediate Similarity	NPC470549
0.8259	Intermediate Similarity	NPC473187
0.8252	Intermediate Similarity	NPC72211
0.8238	Intermediate Similarity	NPC476106
0.8169	Intermediate Similarity	NPC11464
0.8159	Intermediate Similarity	NPC94943
0.8157	Intermediate Similarity	NPC469594
0.8155	Intermediate Similarity	NPC70259
0.8145	Intermediate Similarity	NPC227908
0.8143	Intermediate Similarity	NPC223427
0.8134	Intermediate Similarity	NPC267423
0.8133	Intermediate Similarity	NPC277351
0.8125	Intermediate Similarity	NPC469554
0.8122	Intermediate Similarity	NPC201697
0.8119	Intermediate Similarity	NPC213530
0.8119	Intermediate Similarity	NPC193267
0.8116	Intermediate Similarity	NPC153042
0.8109	Intermediate Similarity	NPC190007
0.8107	Intermediate Similarity	NPC43787
0.8107	Intermediate Similarity	NPC205934
0.8104	Intermediate Similarity	NPC285558
0.81	Intermediate Similarity	NPC179287
0.8086	Intermediate Similarity	NPC329747
0.8075	Intermediate Similarity	NPC470931
0.8075	Intermediate Similarity	NPC475910
0.806	Intermediate Similarity	NPC212535
0.8044	Intermediate Similarity	NPC101543
0.8038	Intermediate Similarity	NPC18487
0.8037	Intermediate Similarity	NPC469589
0.801	Intermediate Similarity	NPC474798
0.8009	Intermediate Similarity	NPC199277
0.8009	Intermediate Similarity	NPC135887
0.7991	Intermediate Similarity	NPC314954
0.7991	Intermediate Similarity	NPC477861
0.7982	Intermediate Similarity	NPC470799
0.7982	Intermediate Similarity	NPC8022
0.7972	Intermediate Similarity	NPC478074
0.7962	Intermediate Similarity	NPC476044
0.7955	Intermediate Similarity	NPC208084
0.7948	Intermediate Similarity	NPC11408
0.7931	Intermediate Similarity	NPC84478
0.7926	Intermediate Similarity	NPC294620
0.7919	Intermediate Similarity	NPC86078
0.7909	Intermediate Similarity	NPC303658
0.788	Intermediate Similarity	NPC208284
0.7879	Intermediate Similarity	NPC217554
0.7844	Intermediate Similarity	NPC316981
0.7844	Intermediate Similarity	NPC26679
0.7838	Intermediate Similarity	NPC150239
0.7834	Intermediate Similarity	NPC167860
0.7834	Intermediate Similarity	NPC123976
0.7828	Intermediate Similarity	NPC184408
0.7818	Intermediate Similarity	NPC183407
0.7808	Intermediate Similarity	NPC266931
0.7804	Intermediate Similarity	NPC245816
0.7804	Intermediate Similarity	NPC476138
0.7788	Intermediate Similarity	NPC185782
0.7778	Intermediate Similarity	NPC246700
0.7778	Intermediate Similarity	NPC284141
0.7768	Intermediate Similarity	NPC280272
0.7768	Intermediate Similarity	NPC162748
0.7759	Intermediate Similarity	NPC89549
0.7753	Intermediate Similarity	NPC274640
0.7748	Intermediate Similarity	NPC247803
0.7746	Intermediate Similarity	NPC329793
0.7746	Intermediate Similarity	NPC11017
0.7745	Intermediate Similarity	NPC475666
0.7743	Intermediate Similarity	NPC200888
0.7734	Intermediate Similarity	NPC72980
0.7734	Intermediate Similarity	NPC88363
0.7723	Intermediate Similarity	NPC310118
0.7718	Intermediate Similarity	NPC473189
0.7717	Intermediate Similarity	NPC87413
0.7714	Intermediate Similarity	NPC307963
0.7714	Intermediate Similarity	NPC475190
0.7711	Intermediate Similarity	NPC474409
0.771	Intermediate Similarity	NPC232727
0.7707	Intermediate Similarity	NPC176127
0.7703	Intermediate Similarity	NPC314552
0.7702	Intermediate Similarity	NPC81939
0.7696	Intermediate Similarity	NPC180504
0.7689	Intermediate Similarity	NPC144452
0.7679	Intermediate Similarity	NPC225279
0.7671	Intermediate Similarity	NPC5145
0.7667	Intermediate Similarity	NPC280964
0.7667	Intermediate Similarity	NPC114335
0.7667	Intermediate Similarity	NPC141915
0.7667	Intermediate Similarity	NPC99666
0.7664	Intermediate Similarity	NPC19872
0.7664	Intermediate Similarity	NPC132385
0.7655	Intermediate Similarity	NPC51388
0.7647	Intermediate Similarity	NPC26543
0.7647	Intermediate Similarity	NPC39500
0.7644	Intermediate Similarity	NPC46580
0.7642	Intermediate Similarity	NPC251090
0.7642	Intermediate Similarity	NPC13880
0.7636	Intermediate Similarity	NPC187501
0.7629	Intermediate Similarity	NPC295228
0.7627	Intermediate Similarity	NPC208522
0.7623	Intermediate Similarity	NPC305984
0.7619	Intermediate Similarity	NPC92111
0.7613	Intermediate Similarity	NPC118228
0.7608	Intermediate Similarity	NPC128751
0.76	Intermediate Similarity	NPC174760
0.7598	Intermediate Similarity	NPC253580
0.7598	Intermediate Similarity	NPC194740
0.7597	Intermediate Similarity	NPC6786
0.7597	Intermediate Similarity	NPC184680
0.7591	Intermediate Similarity	NPC471304
0.7589	Intermediate Similarity	NPC46561
0.7589	Intermediate Similarity	NPC473041
0.7581	Intermediate Similarity	NPC249040
0.758	Intermediate Similarity	NPC39679
0.758	Intermediate Similarity	NPC477111
0.7577	Intermediate Similarity	NPC211416
0.7574	Intermediate Similarity	NPC477066
0.7571	Intermediate Similarity	NPC106833
0.7571	Intermediate Similarity	NPC469497
0.7571	Intermediate Similarity	NPC76748
0.7564	Intermediate Similarity	NPC470785
0.7564	Intermediate Similarity	NPC470784
0.7563	Intermediate Similarity	NPC471891
0.7555	Intermediate Similarity	NPC470126
0.7555	Intermediate Similarity	NPC110151
0.7548	Intermediate Similarity	NPC42591
0.7542	Intermediate Similarity	NPC133609
0.7542	Intermediate Similarity	NPC478081
0.7535	Intermediate Similarity	NPC476167
0.7534	Intermediate Similarity	NPC4687
0.7534	Intermediate Similarity	NPC249583
0.7532	Intermediate Similarity	NPC476451
0.7532	Intermediate Similarity	NPC474688
0.7524	Intermediate Similarity	NPC296527
0.7523	Intermediate Similarity	NPC202605
0.7523	Intermediate Similarity	NPC164374
0.7523	Intermediate Similarity	NPC137929
0.7523	Intermediate Similarity	NPC308137
0.7523	Intermediate Similarity	NPC475070
0.7523	Intermediate Similarity	NPC310211
0.7523	Intermediate Similarity	NPC112206
0.751	Intermediate Similarity	NPC189079
0.75	Intermediate Similarity	NPC475844
0.75	Intermediate Similarity	NPC330009
0.75	Intermediate Similarity	NPC3207
0.75	Intermediate Similarity	NPC176538
0.75	Intermediate Similarity	NPC477110
0.7489	Intermediate Similarity	NPC476287
0.7489	Intermediate Similarity	NPC60621
0.7489	Intermediate Similarity	NPC472111
0.7489	Intermediate Similarity	NPC131486
0.7489	Intermediate Similarity	NPC198503
0.7488	Intermediate Similarity	NPC192315
0.7479	Intermediate Similarity	NPC78609
0.7477	Intermediate Similarity	NPC23294
0.7468	Intermediate Similarity	NPC478082
0.7468	Intermediate Similarity	NPC477067
0.7467	Intermediate Similarity	NPC304926
0.7467	Intermediate Similarity	NPC293151
0.7467	Intermediate Similarity	NPC169402
0.7467	Intermediate Similarity	NPC476041
0.7466	Intermediate Similarity	NPC476116
0.7458	Intermediate Similarity	NPC91868
0.7458	Intermediate Similarity	NPC63971
0.7457	Intermediate Similarity	NPC474701

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 NPC473185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	707
0.2-0.3	867
0.3-0.4	1638
0.4-0.5	2724
0.5-0.6	2016
0.6-0.7	725
0.7-0.8	121
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
0.8286	Intermediate Similarity	NPD7222	Phase 2
0.8199	Intermediate Similarity	NPD7453	Approved
0.8199	Intermediate Similarity	NPD7452	Approved
0.8102	Intermediate Similarity	NPD5903	Approved
0.8102	Intermediate Similarity	NPD5902	Approved
0.8075	Intermediate Similarity	NPD5658	Approved
0.8066	Intermediate Similarity	NPD3003	Approved
0.8009	Intermediate Similarity	NPD7558	Phase 2
0.7915	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD6985	Discontinued
0.7892	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD4502	Phase 2
0.7873	Intermediate Similarity	NPD7194	Discontinued
0.7867	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5612	Discontinued
0.7783	Intermediate Similarity	NPD1768	Approved
0.7731	Intermediate Similarity	NPD5530	Phase 1
0.7714	Intermediate Similarity	NPD1038	Approved
0.7713	Intermediate Similarity	NPD3875	Discontinued
0.7708	Intermediate Similarity	NPD8244	Phase 2
0.7703	Intermediate Similarity	NPD5164	Discontinued
0.7689	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD8364	Approved
0.7683	Intermediate Similarity	NPD8363	Approved
0.7679	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6494	Phase 2
0.7615	Intermediate Similarity	NPD1392	Approved
0.7606	Intermediate Similarity	NPD7948	Phase 1
0.7569	Intermediate Similarity	NPD8403	Phase 1
0.7557	Intermediate Similarity	NPD5936	Approved
0.7557	Intermediate Similarity	NPD5939	Approved
0.7547	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4511	Phase 1
0.7536	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5913	Phase 3
0.7535	Intermediate Similarity	NPD8396	Approved
0.7535	Intermediate Similarity	NPD8395	Approved
0.753	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD4418	Discontinued
0.7512	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7219	Approved
0.7456	Intermediate Similarity	NPD7221	Approved
0.7454	Intermediate Similarity	NPD2175	Phase 3
0.7454	Intermediate Similarity	NPD2177	Approved
0.7454	Intermediate Similarity	NPD2176	Approved
0.7446	Intermediate Similarity	NPD7555	Discontinued
0.7434	Intermediate Similarity	NPD5632	Approved
0.7431	Intermediate Similarity	NPD8466	Approved
0.7431	Intermediate Similarity	NPD8428	Approved
0.7431	Intermediate Similarity	NPD8465	Approved
0.7431	Intermediate Similarity	NPD8467	Approved
0.7431	Intermediate Similarity	NPD8429	Approved
0.7431	Intermediate Similarity	NPD8427	Approved
0.7401	Intermediate Similarity	NPD3763	Approved
0.7399	Intermediate Similarity	NPD5066	Phase 2
0.7399	Intermediate Similarity	NPD5067	Phase 2
0.7376	Intermediate Similarity	NPD6290	Phase 2
0.7371	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3330	Phase 1
0.7364	Intermediate Similarity	NPD7067	Approved
0.7364	Intermediate Similarity	NPD7068	Approved
0.7359	Intermediate Similarity	NPD7603	Discontinued
0.7344	Intermediate Similarity	NPD8358	Approved
0.7343	Intermediate Similarity	NPD6159	Phase 2
0.7342	Intermediate Similarity	NPD2916	Discontinued
0.7333	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD8426	Approved
0.7315	Intermediate Similarity	NPD8459	Approved
0.7315	Intermediate Similarity	NPD8460	Approved
0.7315	Intermediate Similarity	NPD8425	Approved
0.7308	Intermediate Similarity	NPD7479	Phase 2
0.7302	Intermediate Similarity	NPD802	Phase 2
0.7301	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5559	Phase 2
0.7294	Intermediate Similarity	NPD3825	Phase 3
0.7289	Intermediate Similarity	NPD3815	Phase 1
0.7289	Intermediate Similarity	NPD3816	Phase 1
0.7285	Intermediate Similarity	NPD4795	Phase 2
0.728	Intermediate Similarity	NPD7417	Discontinued
0.728	Intermediate Similarity	NPD8284	Discontinued
0.7277	Intermediate Similarity	NPD4885	Approved
0.7268	Intermediate Similarity	NPD1326	Approved
0.7268	Intermediate Similarity	NPD1325	Approved
0.7265	Intermediate Similarity	NPD7671	Approved
0.7265	Intermediate Similarity	NPD7672	Approved
0.7264	Intermediate Similarity	NPD5256	Discontinued
0.7256	Intermediate Similarity	NPD6569	Phase 2
0.7249	Intermediate Similarity	NPD3402	Phase 1
0.7244	Intermediate Similarity	NPD6220	Phase 3
0.7241	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD6742	Phase 2
0.7224	Intermediate Similarity	NPD6743	Phase 2
0.722	Intermediate Similarity	NPD5429	Discontinued
0.7217	Intermediate Similarity	NPD6242	Discontinued
0.7213	Intermediate Similarity	NPD6243	Phase 3
0.7213	Intermediate Similarity	NPD5482	Discontinued
0.7213	Intermediate Similarity	NPD6244	Phase 3
0.7205	Intermediate Similarity	NPD7395	Discontinued
0.7205	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5479	Discontinued
0.7189	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4454	Phase 2
0.7179	Intermediate Similarity	NPD6978	Phase 2
0.7179	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6473	Phase 1
0.7171	Intermediate Similarity	NPD6456	Discontinued
0.7167	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8016	Phase 3
0.7162	Intermediate Similarity	NPD6991	Approved
0.7156	Intermediate Similarity	NPD4204	Approved
0.7156	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4203	Approved
0.7155	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5930	Phase 3
0.7136	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD3746	Discontinued
0.713	Intermediate Similarity	NPD4038	Approved
0.713	Intermediate Similarity	NPD4122	Approved
0.713	Intermediate Similarity	NPD4034	Approved
0.713	Intermediate Similarity	NPD4036	Approved
0.713	Intermediate Similarity	NPD4039	Approved
0.713	Intermediate Similarity	NPD32	Approved
0.713	Intermediate Similarity	NPD4035	Approved
0.713	Intermediate Similarity	NPD4037	Approved
0.713	Intermediate Similarity	NPD31	Approved
0.713	Intermediate Similarity	NPD4033	Approved
0.7123	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7567	Approved
0.7117	Intermediate Similarity	NPD6975	Discontinued
0.7113	Intermediate Similarity	NPD3006	Discontinued
0.7112	Intermediate Similarity	NPD7726	Phase 1
0.7111	Intermediate Similarity	NPD2187	Approved
0.7111	Intermediate Similarity	NPD2189	Approved
0.711	Intermediate Similarity	NPD6590	Discontinued
0.7108	Intermediate Similarity	NPD8091	Phase 3
0.7107	Intermediate Similarity	NPD6716	Phase 1
0.7107	Intermediate Similarity	NPD6517	Phase 3
0.7104	Intermediate Similarity	NPD1739	Approved
0.7104	Intermediate Similarity	NPD1740	Approved
0.7094	Intermediate Similarity	NPD6246	Approved
0.7091	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5488	Discontinued
0.7082	Intermediate Similarity	NPD6736	Discontinued
0.7082	Intermediate Similarity	NPD1856	Discontinued
0.7082	Intermediate Similarity	NPD1954	Phase 1
0.708	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3920	Phase 2
0.7059	Intermediate Similarity	NPD5999	Phase 2
0.7056	Intermediate Similarity	NPD4429	Discontinued
0.7052	Intermediate Similarity	NPD6531	Approved
0.7052	Intermediate Similarity	NPD6530	Approved
0.7049	Intermediate Similarity	NPD4350	Approved
0.7049	Intermediate Similarity	NPD4349	Approved
0.7046	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5003	Discontinued
0.7043	Intermediate Similarity	NPD6643	Discontinued
0.7042	Intermediate Similarity	NPD7853	Phase 2
0.7034	Intermediate Similarity	NPD7994	Phase 2
0.7034	Intermediate Similarity	NPD3259	Approved
0.7033	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3921	Approved
0.7018	Intermediate Similarity	NPD3922	Approved
0.7018	Intermediate Similarity	NPD3923	Approved
0.7018	Intermediate Similarity	NPD5416	Discontinued
0.7018	Intermediate Similarity	NPD3924	Approved
0.7016	Intermediate Similarity	NPD7859	Phase 2
0.7016	Intermediate Similarity	NPD7659	Discontinued
0.7015	Intermediate Similarity	NPD8489	Phase 1
0.7012	Intermediate Similarity	NPD7955	Approved
0.7012	Intermediate Similarity	NPD7956	Approved
0.7008	Intermediate Similarity	NPD7413	Phase 3
0.7	Intermediate Similarity	NPD2951	Discontinued
0.7	Intermediate Similarity	NPD6961	Discontinued
0.7	Intermediate Similarity	NPD5512	Phase 3
0.6996	Remote Similarity	NPD6790	Phase 1
0.6996	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD7675	Phase 3
0.6992	Remote Similarity	NPD7426	Phase 1
0.6992	Remote Similarity	NPD7674	Phase 3
0.6987	Remote Similarity	NPD7069	Discontinued
0.6987	Remote Similarity	NPD6202	Discontinued
0.6983	Remote Similarity	NPD6750	Phase 2

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