NPASS Compound

Structure

NPC473183 OpenBabel07101718292D 33 38 0 0 0 0 0 0 0 0999 V2000 0.0511 -2.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7256 4.1282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1146 -0.7816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2834 0.0526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9806 -0.2816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1789 1.0471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2486 -0.2816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4744 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9806 0.7184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2653 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5109 1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3298 3.0056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0714 1.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0769 2.0920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2486 0.7184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5608 -0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5054 1.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1146 1.2184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4563 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3244 3.1101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9122 2.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9067 2.1965 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 1.0739 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7311 4.0236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 7 2 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 18 2 0 0 0 0 9 19 2 0 0 0 0 10 22 2 0 0 0 0 11 23 2 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 24 2 0 0 0 0 15 17 1 0 0 0 0 15 30 1 0 0 0 0 16 27 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 25 2 0 0 0 0 21 26 2 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 0 0 0 0 25 29 1 0 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 27 28 2 0 0 0 0 27 31 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.18
Volume:	458.232
LogP:	6.065
LogD:	4.389
LogS:	-6.19
# Rotatable Bonds:	4
TPSA:	59.41
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	2.578
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.424
MDCK Permeability:	2.3291375327971764e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.849
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	97.50978088378906%
Volume Distribution (VD):	0.605
Pgp-substrate:	1.3356703519821167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.163
CYP2C9-inhibitor:	0.91
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.825
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.619
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	6.683
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.178
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.846
AMES Toxicity:	0.894
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.761
Carcinogencity:	0.925
Eye Corrosion:	0.003
Eye Irritation:	0.719
Respiratory Toxicity:	0.831

Download Data

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

Natural Product: NPC473183

Natural Product ID:	NPC473183
*Common Name:**	QYBRVLDQGNFHFN-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QYBRVLDQGNFHFN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H24N2O3/c1-16-12-21-19-9-5-7-11-23(19)30(26(21)28(33-3)27(16)31)15-17-13-20-18-8-4-6-10-22(18)29-25(20)24(14-17)32-2/h4-14,29,31H,15H2,1-3H3
SMILES:	COc1c(O)c(C)cc2c1n(Cc1cc(OC)c3c(c1)c1ccccc1[nH]3)c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633079
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[510361]

☑ 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 NPC473183 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	664
0.1-0.2	4186
0.2-0.3	13145
0.3-0.4	6616
0.4-0.5	12568
0.5-0.6	3411
0.6-0.7	1607
0.7-0.8	445
0.8-0.85	45
0.85-0.9	3
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC473184
0.9617	High Similarity	NPC473185
0.9484	High Similarity	NPC473182
0.9282	High Similarity	NPC473179
0.9057	High Similarity	NPC132642
0.9032	High Similarity	NPC475253
0.8995	High Similarity	NPC94157
0.8591	High Similarity	NPC202503
0.8545	High Similarity	NPC199667
0.8498	Intermediate Similarity	NPC473181
0.8491	Intermediate Similarity	NPC473188
0.8489	Intermediate Similarity	NPC277351
0.8465	Intermediate Similarity	NPC473180
0.8409	Intermediate Similarity	NPC477532
0.8389	Intermediate Similarity	NPC199277
0.8389	Intermediate Similarity	NPC135887
0.8364	Intermediate Similarity	NPC477533
0.8348	Intermediate Similarity	NPC252251
0.8326	Intermediate Similarity	NPC209769
0.8325	Intermediate Similarity	NPC70956
0.8325	Intermediate Similarity	NPC243834
0.8274	Intermediate Similarity	NPC477531
0.8246	Intermediate Similarity	NPC39370
0.8238	Intermediate Similarity	NPC473186
0.8233	Intermediate Similarity	NPC193777
0.823	Intermediate Similarity	NPC209174
0.8225	Intermediate Similarity	NPC217554
0.8224	Intermediate Similarity	NPC470930
0.8211	Intermediate Similarity	NPC316981
0.8174	Intermediate Similarity	NPC266931
0.8174	Intermediate Similarity	NPC471080
0.8174	Intermediate Similarity	NPC469592
0.816	Intermediate Similarity	NPC128823
0.8139	Intermediate Similarity	NPC11408
0.8131	Intermediate Similarity	NPC475085
0.8131	Intermediate Similarity	NPC291535
0.8131	Intermediate Similarity	NPC475112
0.812	Intermediate Similarity	NPC284141
0.8093	Intermediate Similarity	NPC475774
0.8091	Intermediate Similarity	NPC89549
0.8057	Intermediate Similarity	NPC131017
0.8045	Intermediate Similarity	NPC48353
0.8027	Intermediate Similarity	NPC469594
0.8018	Intermediate Similarity	NPC170114
0.8009	Intermediate Similarity	NPC162484
0.799	Intermediate Similarity	NPC242928
0.7974	Intermediate Similarity	NPC473187
0.7973	Intermediate Similarity	NPC470549
0.7965	Intermediate Similarity	NPC280272
0.7944	Intermediate Similarity	NPC72211
0.7939	Intermediate Similarity	NPC200888
0.7936	Intermediate Similarity	NPC476106
0.7909	Intermediate Similarity	NPC469589
0.7883	Intermediate Similarity	NPC112206
0.7883	Intermediate Similarity	NPC202605
0.7873	Intermediate Similarity	NPC11464
0.786	Intermediate Similarity	NPC227908
0.785	Intermediate Similarity	NPC70259
0.7847	Intermediate Similarity	NPC94943
0.7846	Intermediate Similarity	NPC132385
0.7845	Intermediate Similarity	NPC469554
0.7844	Intermediate Similarity	NPC223427
0.7834	Intermediate Similarity	NPC267423
0.7832	Intermediate Similarity	NPC193267
0.7832	Intermediate Similarity	NPC213530
0.7828	Intermediate Similarity	NPC201697
0.7821	Intermediate Similarity	NPC295228
0.7817	Intermediate Similarity	NPC179287
0.7814	Intermediate Similarity	NPC153042
0.7808	Intermediate Similarity	NPC285558
0.7804	Intermediate Similarity	NPC43787
0.7804	Intermediate Similarity	NPC205934
0.7799	Intermediate Similarity	NPC190007
0.7792	Intermediate Similarity	NPC476997
0.7788	Intermediate Similarity	NPC329747
0.7783	Intermediate Similarity	NPC475910
0.7783	Intermediate Similarity	NPC470931
0.7773	Intermediate Similarity	NPC211416
0.7768	Intermediate Similarity	NPC101543
0.7759	Intermediate Similarity	NPC476998
0.7759	Intermediate Similarity	NPC476996
0.7751	Intermediate Similarity	NPC212535
0.7742	Intermediate Similarity	NPC18487
0.7729	Intermediate Similarity	NPC118121
0.7722	Intermediate Similarity	NPC477861
0.7716	Intermediate Similarity	NPC314954
0.7716	Intermediate Similarity	NPC476994
0.7709	Intermediate Similarity	NPC173080
0.7703	Intermediate Similarity	NPC474798
0.7699	Intermediate Similarity	NPC470799
0.7699	Intermediate Similarity	NPC8022
0.7689	Intermediate Similarity	NPC478074
0.7675	Intermediate Similarity	NPC208084
0.7671	Intermediate Similarity	NPC476044
0.7644	Intermediate Similarity	NPC294620
0.7642	Intermediate Similarity	NPC86078
0.7636	Intermediate Similarity	NPC66815
0.7632	Intermediate Similarity	NPC303658
0.763	Intermediate Similarity	NPC84478
0.7613	Intermediate Similarity	NPC304183
0.76	Intermediate Similarity	NPC208284
0.7598	Intermediate Similarity	NPC46451
0.7568	Intermediate Similarity	NPC36229
0.7568	Intermediate Similarity	NPC476581
0.7568	Intermediate Similarity	NPC16452
0.7566	Intermediate Similarity	NPC26679
0.7565	Intermediate Similarity	NPC150239
0.7563	Intermediate Similarity	NPC184680
0.7556	Intermediate Similarity	NPC167860
0.7556	Intermediate Similarity	NPC123976
0.7555	Intermediate Similarity	NPC23614
0.7555	Intermediate Similarity	NPC184408
0.7555	Intermediate Similarity	NPC100079
0.7555	Intermediate Similarity	NPC204446
0.7544	Intermediate Similarity	NPC183407
0.7533	Intermediate Similarity	NPC162530
0.7531	Intermediate Similarity	NPC470785
0.7523	Intermediate Similarity	NPC245816
0.7523	Intermediate Similarity	NPC476138
0.7522	Intermediate Similarity	NPC148409
0.7511	Intermediate Similarity	NPC185782
0.75	Intermediate Similarity	NPC41501
0.75	Intermediate Similarity	NPC162748
0.75	Intermediate Similarity	NPC122463
0.75	Intermediate Similarity	NPC270515
0.749	Intermediate Similarity	NPC476995
0.749	Intermediate Similarity	NPC475666
0.7489	Intermediate Similarity	NPC96405
0.7489	Intermediate Similarity	NPC296482
0.7489	Intermediate Similarity	NPC171409
0.7489	Intermediate Similarity	NPC53069
0.7489	Intermediate Similarity	NPC202768
0.7489	Intermediate Similarity	NPC203168
0.7489	Intermediate Similarity	NPC274640
0.7488	Intermediate Similarity	NPC246700
0.7478	Intermediate Similarity	NPC247803
0.7478	Intermediate Similarity	NPC219664
0.7477	Intermediate Similarity	NPC326634
0.7471	Intermediate Similarity	NPC237901
0.7471	Intermediate Similarity	NPC195788
0.7469	Intermediate Similarity	NPC475844
0.7469	Intermediate Similarity	NPC472066
0.7469	Intermediate Similarity	NPC472067
0.7469	Intermediate Similarity	NPC472031
0.7466	Intermediate Similarity	NPC329793
0.7466	Intermediate Similarity	NPC11017
0.7458	Intermediate Similarity	NPC470784
0.7457	Intermediate Similarity	NPC310118
0.7449	Intermediate Similarity	NPC81939
0.7447	Intermediate Similarity	NPC110151
0.7445	Intermediate Similarity	NPC87413
0.7441	Intermediate Similarity	NPC88363
0.7441	Intermediate Similarity	NPC72980
0.7437	Intermediate Similarity	NPC180504
0.7435	Intermediate Similarity	NPC314552
0.7432	Intermediate Similarity	NPC31930
0.7432	Intermediate Similarity	NPC232727
0.7431	Intermediate Similarity	NPC307963
0.7431	Intermediate Similarity	NPC475190
0.743	Intermediate Similarity	NPC473189
0.7426	Intermediate Similarity	NPC201508
0.7425	Intermediate Similarity	NPC144452
0.7424	Intermediate Similarity	NPC235076
0.7418	Intermediate Similarity	NPC176127
0.7416	Intermediate Similarity	NPC474409
0.7414	Intermediate Similarity	NPC225279
0.7412	Intermediate Similarity	NPC251160
0.7404	Intermediate Similarity	NPC214980
0.7401	Intermediate Similarity	NPC5145
0.7398	Intermediate Similarity	NPC26543
0.7393	Intermediate Similarity	NPC51388
0.7388	Intermediate Similarity	NPC472068
0.7387	Intermediate Similarity	NPC19872
0.7385	Intermediate Similarity	NPC280964
0.7385	Intermediate Similarity	NPC99666
0.7385	Intermediate Similarity	NPC114335
0.7385	Intermediate Similarity	NPC141915
0.738	Intermediate Similarity	NPC39500
0.738	Intermediate Similarity	NPC271215
0.738	Intermediate Similarity	NPC149471
0.7377	Intermediate Similarity	NPC208522
0.7368	Intermediate Similarity	NPC187501
0.7364	Intermediate Similarity	NPC13880
0.7364	Intermediate Similarity	NPC251090
0.7361	Intermediate Similarity	NPC46580
0.7359	Intermediate Similarity	NPC305984
0.7356	Intermediate Similarity	NPC260909
0.7348	Intermediate Similarity	NPC118228
0.7344	Intermediate Similarity	NPC6786
0.7342	Intermediate Similarity	NPC476578
0.7342	Intermediate Similarity	NPC4071
0.7342	Intermediate Similarity	NPC194740
0.7342	Intermediate Similarity	NPC253580
0.7342	Intermediate Similarity	NPC476582
0.7339	Intermediate Similarity	NPC174760
0.7339	Intermediate Similarity	NPC174049
0.7339	Intermediate Similarity	NPC92111
0.7328	Intermediate Similarity	NPC46561
0.7328	Intermediate Similarity	NPC473041
0.7327	Intermediate Similarity	NPC128751

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 NPC473183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	703
0.2-0.3	935
0.3-0.4	1767
0.4-0.5	2731
0.5-0.6	1952
0.6-0.7	636
0.7-0.8	94
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
0.8387	Intermediate Similarity	NPD5902	Approved
0.8387	Intermediate Similarity	NPD5903	Approved
0.8279	Intermediate Similarity	NPD5658	Approved
0.8255	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD3003	Approved
0.7982	Intermediate Similarity	NPD7222	Phase 2
0.7965	Intermediate Similarity	NPD7558	Phase 2
0.79	Intermediate Similarity	NPD7453	Approved
0.79	Intermediate Similarity	NPD7452	Approved
0.7867	Intermediate Similarity	NPD6985	Discontinued
0.7854	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD7194	Discontinued
0.7811	Intermediate Similarity	NPD6494	Phase 2
0.7778	Intermediate Similarity	NPD5612	Discontinued
0.7742	Intermediate Similarity	NPD1768	Approved
0.7649	Intermediate Similarity	NPD8363	Approved
0.7649	Intermediate Similarity	NPD8364	Approved
0.76	Intermediate Similarity	NPD4502	Phase 2
0.7598	Intermediate Similarity	NPD3763	Approved
0.7594	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1392	Approved
0.7489	Intermediate Similarity	NPD3816	Phase 1
0.7489	Intermediate Similarity	NPD3815	Phase 1
0.7471	Intermediate Similarity	NPD8465	Approved
0.7471	Intermediate Similarity	NPD8429	Approved
0.7471	Intermediate Similarity	NPD8427	Approved
0.7471	Intermediate Similarity	NPD8428	Approved
0.7471	Intermediate Similarity	NPD8467	Approved
0.7471	Intermediate Similarity	NPD8466	Approved
0.7468	Intermediate Similarity	NPD4885	Approved
0.746	Intermediate Similarity	NPD8244	Phase 2
0.7455	Intermediate Similarity	NPD5530	Phase 1
0.7446	Intermediate Similarity	NPD3875	Discontinued
0.7435	Intermediate Similarity	NPD5164	Discontinued
0.7431	Intermediate Similarity	NPD1038	Approved
0.7425	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6244	Phase 3
0.7398	Intermediate Similarity	NPD6243	Phase 3
0.7368	Intermediate Similarity	NPD5067	Phase 2
0.7368	Intermediate Similarity	NPD5066	Phase 2
0.7366	Intermediate Similarity	NPD6517	Phase 3
0.7356	Intermediate Similarity	NPD8460	Approved
0.7356	Intermediate Similarity	NPD8459	Approved
0.7356	Intermediate Similarity	NPD8426	Approved
0.7356	Intermediate Similarity	NPD8425	Approved
0.7339	Intermediate Similarity	NPD5930	Phase 3
0.733	Intermediate Similarity	NPD7948	Phase 1
0.7328	Intermediate Similarity	NPD5632	Approved
0.7301	Intermediate Similarity	NPD8403	Phase 1
0.7293	Intermediate Similarity	NPD5939	Approved
0.7293	Intermediate Similarity	NPD5936	Approved
0.7291	Intermediate Similarity	NPD8091	Phase 3
0.7277	Intermediate Similarity	NPD1954	Phase 1
0.7277	Intermediate Similarity	NPD3920	Phase 2
0.7277	Intermediate Similarity	NPD4511	Phase 1
0.7273	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8396	Approved
0.7265	Intermediate Similarity	NPD8395	Approved
0.726	Intermediate Similarity	NPD5913	Phase 3
0.726	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4418	Discontinued
0.724	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD3921	Approved
0.7227	Intermediate Similarity	NPD3922	Approved
0.7227	Intermediate Similarity	NPD3923	Approved
0.7227	Intermediate Similarity	NPD3924	Approved
0.721	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7221	Approved
0.7203	Intermediate Similarity	NPD7219	Approved
0.72	Intermediate Similarity	NPD7859	Phase 2
0.7197	Intermediate Similarity	NPD7555	Discontinued
0.7194	Intermediate Similarity	NPD7956	Approved
0.7194	Intermediate Similarity	NPD7955	Approved
0.7188	Intermediate Similarity	NPD2175	Phase 3
0.7188	Intermediate Similarity	NPD2176	Approved
0.7188	Intermediate Similarity	NPD2177	Approved
0.716	Intermediate Similarity	NPD4454	Phase 2
0.7149	Intermediate Similarity	NPD4080	Discontinued
0.7148	Intermediate Similarity	NPD6456	Discontinued
0.7143	Intermediate Similarity	NPD7719	Discontinued
0.7143	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7067	Approved
0.7126	Intermediate Similarity	NPD7068	Approved
0.7125	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6964	Approved
0.7119	Intermediate Similarity	NPD6963	Approved
0.7118	Intermediate Similarity	NPD6290	Phase 2
0.7113	Intermediate Similarity	NPD7603	Discontinued
0.7112	Intermediate Similarity	NPD3330	Phase 1
0.7108	Intermediate Similarity	NPD8358	Approved
0.7097	Intermediate Similarity	NPD6230	Discontinued
0.7087	Intermediate Similarity	NPD7169	Suspended
0.7087	Intermediate Similarity	NPD2916	Discontinued
0.7083	Intermediate Similarity	NPD6978	Phase 2
0.7083	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6159	Phase 2
0.7069	Intermediate Similarity	NPD4131	Phase 3
0.7064	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8489	Phase 1
0.7054	Intermediate Similarity	NPD8284	Discontinued
0.7054	Intermediate Similarity	NPD7803	Approved
0.7054	Intermediate Similarity	NPD5559	Phase 2
0.7051	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7417	Discontinued
0.7042	Intermediate Similarity	NPD4083	Discontinued
0.704	Intermediate Similarity	NPD802	Phase 2
0.7037	Intermediate Similarity	NPD7479	Phase 2
0.7035	Intermediate Similarity	NPD3825	Phase 3
0.7031	Intermediate Similarity	NPD6530	Approved
0.7031	Intermediate Similarity	NPD6531	Approved
0.7031	Intermediate Similarity	NPD4795	Phase 2
0.7025	Intermediate Similarity	NPD8512	Phase 3
0.7016	Intermediate Similarity	NPD6716	Phase 1
0.7013	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7672	Approved
0.7013	Intermediate Similarity	NPD7671	Approved
0.7004	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD3402	Phase 1
0.7004	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5256	Discontinued
0.6996	Remote Similarity	NPD6742	Phase 2
0.6996	Remote Similarity	NPD6220	Phase 3
0.6996	Remote Similarity	NPD6743	Phase 2
0.6996	Remote Similarity	NPD6569	Phase 2
0.6995	Remote Similarity	NPD1326	Approved
0.6995	Remote Similarity	NPD1325	Approved
0.6984	Remote Similarity	NPD5482	Discontinued
0.6975	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6242	Discontinued
0.6971	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7674	Phase 3
0.6971	Remote Similarity	NPD7675	Phase 3
0.6971	Remote Similarity	NPD7426	Phase 1
0.697	Remote Similarity	NPD5429	Discontinued
0.6964	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6750	Phase 2
0.6962	Remote Similarity	NPD7395	Discontinued
0.6962	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD5479	Discontinued
0.6955	Remote Similarity	NPD7181	Phase 3
0.6948	Remote Similarity	NPD6473	Phase 1
0.6942	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8442	Discontinued
0.6939	Remote Similarity	NPD4373	Phase 2
0.6935	Remote Similarity	NPD8016	Phase 3
0.6935	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6455	Phase 3
0.6933	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3343	Phase 3
0.6917	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6991	Approved
0.6907	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7708	Approved
0.6898	Remote Similarity	NPD3746	Discontinued
0.6895	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4204	Approved
0.6895	Remote Similarity	NPD4203	Approved
0.6892	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5022	Discontinued
0.6885	Remote Similarity	NPD7567	Approved
0.6883	Remote Similarity	NPD4033	Approved
0.6883	Remote Similarity	NPD4036	Approved
0.6883	Remote Similarity	NPD4035	Approved
0.6883	Remote Similarity	NPD4037	Approved
0.6883	Remote Similarity	NPD3006	Discontinued
0.6883	Remote Similarity	NPD31	Approved
0.6883	Remote Similarity	NPD4122	Approved
0.6883	Remote Similarity	NPD4038	Approved
0.6883	Remote Similarity	NPD32	Approved
0.6883	Remote Similarity	NPD4039	Approved
0.6883	Remote Similarity	NPD4034	Approved
0.688	Remote Similarity	NPD4876	Phase 3
0.688	Remote Similarity	NPD4875	Phase 3
0.6878	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7726	Phase 1
0.6872	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4605	Approved
0.6872	Remote Similarity	NPD4604	Approved
0.687	Remote Similarity	NPD6975	Discontinued
0.6867	Remote Similarity	NPD2187	Approved
0.6867	Remote Similarity	NPD5905	Phase 1
0.6867	Remote Similarity	NPD2189	Approved
0.6865	Remote Similarity	NPD5488	Discontinued
0.6864	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6246	Approved
0.6859	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD6590	Discontinued
0.6856	Remote Similarity	NPD1740	Approved
0.6856	Remote Similarity	NPD1739	Approved
0.685	Remote Similarity	NPD6525	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