NPASS Compound

Structure

NPC473182 OpenBabel07101718292D 33 38 0 0 0 0 0 0 0 0999 V2000 -0.2257 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4616 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0787 2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2598 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 2.9962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 -0.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7295 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1314 -0.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 -0.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9975 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2543 1.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5334 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6611 2.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5334 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7295 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9975 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 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 1.5823 0.9135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6556 2.0827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -1.0181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5955 1.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 18 2 0 0 0 0 7 21 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 20 2 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 27 2 0 0 0 0 17 24 2 0 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 25 1 0 0 0 0 21 30 1 0 0 0 0 22 29 1 0 0 0 0 23 26 2 0 0 0 0 23 32 1 0 0 0 0 24 26 1 0 0 0 0 25 28 2 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 28 1 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:	6.217
LogD:	4.317
LogS:	-5.061
# Rotatable Bonds:	4
TPSA:	70.27
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	2.662
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:	-5.634
MDCK Permeability:	1.0023281902249437e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.4668960571289%
Volume Distribution (VD):	0.593
Pgp-substrate:	2.6951282024383545%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.888
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.917
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.608
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	4.726
Half-life (T1/2):	0.224

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.862
Rat Oral Acute Toxicity:	0.662
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.921
Carcinogencity:	0.926
Eye Corrosion:	0.003
Eye Irritation:	0.878
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC473182

Natural Product ID:	NPC473182
*Common Name:**	VREXQYWDSJMYRW-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VREXQYWDSJMYRW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H24N2O3/c1-15-12-20-19-14-16(8-10-22(19)29-25(20)28(33-3)27(15)31)13-17-9-11-23(32-2)26-24(17)18-6-4-5-7-21(18)30-26/h4-12,14,29-31H,13H2,1-3H3
SMILES:	COc1c(O)c(C)cc2c1[nH]c1c2cc(cc1)Cc1ccc(c2c1c1ccccc1[nH]2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633078
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[534190]

☑ 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 NPC473182 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	675
0.1-0.2	3948
0.2-0.3	13516
0.3-0.4	5631
0.4-0.5	13370
0.5-0.6	3858
0.6-0.7	1330
0.7-0.8	315
0.8-0.85	38
0.85-0.9	10
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9484	High Similarity	NPC473183
0.9481	High Similarity	NPC473184
0.9417	High Similarity	NPC473179
0.9108	High Similarity	NPC473185
0.9061	High Similarity	NPC202503
0.9029	High Similarity	NPC199667
0.8981	High Similarity	NPC473181
0.8942	High Similarity	NPC473180
0.8716	High Similarity	NPC252251
0.8636	High Similarity	NPC477531
0.8612	High Similarity	NPC193777
0.8591	High Similarity	NPC209174
0.8565	High Similarity	NPC132642
0.8552	High Similarity	NPC475253
0.8522	High Similarity	NPC473188
0.852	High Similarity	NPC277351
0.8498	Intermediate Similarity	NPC94157
0.8447	Intermediate Similarity	NPC243834
0.8447	Intermediate Similarity	NPC70956
0.8443	Intermediate Similarity	NPC209769
0.844	Intermediate Similarity	NPC477532
0.8426	Intermediate Similarity	NPC89549
0.8421	Intermediate Similarity	NPC199277
0.8421	Intermediate Similarity	NPC135887
0.8411	Intermediate Similarity	NPC48353
0.8341	Intermediate Similarity	NPC470930
0.8288	Intermediate Similarity	NPC200888
0.8278	Intermediate Similarity	NPC128823
0.8246	Intermediate Similarity	NPC475112
0.8246	Intermediate Similarity	NPC291535
0.8246	Intermediate Similarity	NPC475085
0.8186	Intermediate Similarity	NPC201697
0.8182	Intermediate Similarity	NPC153042
0.8107	Intermediate Similarity	NPC242928
0.8095	Intermediate Similarity	NPC217554
0.8086	Intermediate Similarity	NPC131017
0.8057	Intermediate Similarity	NPC72211
0.8047	Intermediate Similarity	NPC476106
0.8037	Intermediate Similarity	NPC162484
0.8028	Intermediate Similarity	NPC267423
0.8009	Intermediate Similarity	NPC11408
0.8	Intermediate Similarity	NPC473187
0.7991	Intermediate Similarity	NPC284141
0.7982	Intermediate Similarity	NPC86078
0.7982	Intermediate Similarity	NPC477533
0.7963	Intermediate Similarity	NPC304183
0.7962	Intermediate Similarity	NPC70259
0.7961	Intermediate Similarity	NPC94943
0.792	Intermediate Similarity	NPC179287
0.7915	Intermediate Similarity	NPC43787
0.7915	Intermediate Similarity	NPC205934
0.7913	Intermediate Similarity	NPC190007
0.7909	Intermediate Similarity	NPC316981
0.7895	Intermediate Similarity	NPC274640
0.7873	Intermediate Similarity	NPC471080
0.7873	Intermediate Similarity	NPC469592
0.7873	Intermediate Similarity	NPC266931
0.787	Intermediate Similarity	NPC223427
0.7869	Intermediate Similarity	NPC132385
0.7864	Intermediate Similarity	NPC212535
0.7863	Intermediate Similarity	NPC475844
0.7847	Intermediate Similarity	NPC246700
0.7832	Intermediate Similarity	NPC280272
0.7832	Intermediate Similarity	NPC144452
0.7828	Intermediate Similarity	NPC294620
0.7822	Intermediate Similarity	NPC225279
0.7816	Intermediate Similarity	NPC474798
0.7808	Intermediate Similarity	NPC470931
0.7807	Intermediate Similarity	NPC227908
0.7802	Intermediate Similarity	NPC39370
0.7797	Intermediate Similarity	NPC51388
0.7797	Intermediate Similarity	NPC211416
0.7792	Intermediate Similarity	NPC473186
0.7778	Intermediate Similarity	NPC476044
0.7778	Intermediate Similarity	NPC208084
0.7768	Intermediate Similarity	NPC314552
0.7767	Intermediate Similarity	NPC18487
0.7753	Intermediate Similarity	NPC118121
0.7742	Intermediate Similarity	NPC66815
0.7733	Intermediate Similarity	NPC469594
0.7723	Intermediate Similarity	NPC170114
0.7706	Intermediate Similarity	NPC475774
0.7699	Intermediate Similarity	NPC148409
0.7679	Intermediate Similarity	NPC470549
0.7678	Intermediate Similarity	NPC128751
0.7672	Intermediate Similarity	NPC474688
0.7665	Intermediate Similarity	NPC150239
0.766	Intermediate Similarity	NPC6786
0.7655	Intermediate Similarity	NPC173080
0.7655	Intermediate Similarity	NPC184408
0.7653	Intermediate Similarity	NPC280964
0.7653	Intermediate Similarity	NPC141915
0.7653	Intermediate Similarity	NPC114335
0.7642	Intermediate Similarity	NPC106833
0.7642	Intermediate Similarity	NPC469497
0.7623	Intermediate Similarity	NPC208284
0.7617	Intermediate Similarity	NPC295228
0.7611	Intermediate Similarity	NPC293151
0.7597	Intermediate Similarity	NPC474701
0.7595	Intermediate Similarity	NPC41501
0.7591	Intermediate Similarity	NPC285558
0.7589	Intermediate Similarity	NPC112206
0.7589	Intermediate Similarity	NPC202605
0.7578	Intermediate Similarity	NPC11464
0.7577	Intermediate Similarity	NPC247803
0.7577	Intermediate Similarity	NPC204446
0.7571	Intermediate Similarity	NPC84478
0.7569	Intermediate Similarity	NPC329747
0.7568	Intermediate Similarity	NPC475910
0.7564	Intermediate Similarity	NPC469554
0.7556	Intermediate Similarity	NPC478074
0.7556	Intermediate Similarity	NPC162530
0.7545	Intermediate Similarity	NPC87413
0.7544	Intermediate Similarity	NPC213530
0.7544	Intermediate Similarity	NPC193267
0.7542	Intermediate Similarity	NPC160898
0.7536	Intermediate Similarity	NPC473189
0.7535	Intermediate Similarity	NPC475190
0.7521	Intermediate Similarity	NPC270515
0.7511	Intermediate Similarity	NPC203168
0.7511	Intermediate Similarity	NPC164374
0.7511	Intermediate Similarity	NPC137929
0.7511	Intermediate Similarity	NPC476997
0.75	Intermediate Similarity	NPC219664
0.7489	Intermediate Similarity	NPC11017
0.7489	Intermediate Similarity	NPC101543
0.7479	Intermediate Similarity	NPC476998
0.7479	Intermediate Similarity	NPC476996
0.7478	Intermediate Similarity	NPC39500
0.7469	Intermediate Similarity	NPC208522
0.7467	Intermediate Similarity	NPC187501
0.7467	Intermediate Similarity	NPC46451
0.7464	Intermediate Similarity	NPC88363
0.7455	Intermediate Similarity	NPC469589
0.7446	Intermediate Similarity	NPC122463
0.7445	Intermediate Similarity	NPC235076
0.7445	Intermediate Similarity	NPC118228
0.744	Intermediate Similarity	NPC474409
0.7436	Intermediate Similarity	NPC476994
0.7435	Intermediate Similarity	NPC174760
0.7424	Intermediate Similarity	NPC23614
0.7424	Intermediate Similarity	NPC303658
0.7424	Intermediate Similarity	NPC100079
0.7418	Intermediate Similarity	NPC204385
0.7412	Intermediate Similarity	NPC470799
0.7412	Intermediate Similarity	NPC8022
0.7411	Intermediate Similarity	NPC39679
0.7404	Intermediate Similarity	NPC312872
0.7381	Intermediate Similarity	NPC72980
0.7371	Intermediate Similarity	NPC42591
0.7366	Intermediate Similarity	NPC4687
0.7366	Intermediate Similarity	NPC249583
0.7357	Intermediate Similarity	NPC308137
0.7357	Intermediate Similarity	NPC310211
0.7357	Intermediate Similarity	NPC251160
0.7348	Intermediate Similarity	NPC46561
0.7347	Intermediate Similarity	NPC472031
0.7347	Intermediate Similarity	NPC472067
0.7347	Intermediate Similarity	NPC472066
0.7345	Intermediate Similarity	NPC167860
0.7345	Intermediate Similarity	NPC123976
0.7336	Intermediate Similarity	NPC183407
0.7336	Intermediate Similarity	NPC3207
0.7328	Intermediate Similarity	NPC280799
0.7328	Intermediate Similarity	NPC198503
0.7313	Intermediate Similarity	NPC9894
0.7313	Intermediate Similarity	NPC23294
0.7309	Intermediate Similarity	NPC245816
0.7309	Intermediate Similarity	NPC476138
0.7304	Intermediate Similarity	NPC169402
0.7303	Intermediate Similarity	NPC477861
0.7293	Intermediate Similarity	NPC116238
0.7292	Intermediate Similarity	NPC184680
0.7288	Intermediate Similarity	NPC314954
0.7281	Intermediate Similarity	NPC26679
0.7277	Intermediate Similarity	NPC36229
0.7277	Intermediate Similarity	NPC214980
0.7277	Intermediate Similarity	NPC476581
0.7277	Intermediate Similarity	NPC176127
0.7277	Intermediate Similarity	NPC16452
0.7269	Intermediate Similarity	NPC303951
0.7269	Intermediate Similarity	NPC132329
0.7269	Intermediate Similarity	NPC188420
0.7265	Intermediate Similarity	NPC472068
0.7264	Intermediate Similarity	NPC478032
0.7261	Intermediate Similarity	NPC470785
0.7257	Intermediate Similarity	NPC18348
0.7256	Intermediate Similarity	NPC276674
0.7256	Intermediate Similarity	NPC33902
0.7249	Intermediate Similarity	NPC474594
0.7249	Intermediate Similarity	NPC271215
0.7249	Intermediate Similarity	NPC149471
0.7246	Intermediate Similarity	NPC470126
0.723	Intermediate Similarity	NPC206201
0.7227	Intermediate Similarity	NPC201508
0.7225	Intermediate Similarity	NPC185782
0.7224	Intermediate Similarity	NPC475666
0.722	Intermediate Similarity	NPC195788
0.722	Intermediate Similarity	NPC232727
0.722	Intermediate Similarity	NPC237901

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 NPC473182 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	743
0.2-0.3	988
0.3-0.4	1849
0.4-0.5	2856
0.5-0.6	1769
0.6-0.7	501
0.7-0.8	68
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5902	Approved
0.8165	Intermediate Similarity	NPD5903	Approved
0.7972	Intermediate Similarity	NPD5658	Approved
0.7878	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3003	Approved
0.7768	Intermediate Similarity	NPD5164	Discontinued
0.7703	Intermediate Similarity	NPD4502	Phase 2
0.7682	Intermediate Similarity	NPD7558	Phase 2
0.7682	Intermediate Similarity	NPD6494	Phase 2
0.7577	Intermediate Similarity	NPD6985	Discontinued
0.7544	Intermediate Similarity	NPD7194	Discontinued
0.7523	Intermediate Similarity	NPD7222	Phase 2
0.7523	Intermediate Similarity	NPD1768	Approved
0.7522	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD5612	Discontinued
0.748	Intermediate Similarity	NPD8244	Phase 2
0.7477	Intermediate Similarity	NPD5530	Phase 1
0.7467	Intermediate Similarity	NPD3763	Approved
0.7464	Intermediate Similarity	NPD3920	Phase 2
0.7444	Intermediate Similarity	NPD7452	Approved
0.7444	Intermediate Similarity	NPD7453	Approved
0.7391	Intermediate Similarity	NPD8363	Approved
0.7391	Intermediate Similarity	NPD8364	Approved
0.7389	Intermediate Similarity	NPD5936	Approved
0.7389	Intermediate Similarity	NPD5939	Approved
0.7376	Intermediate Similarity	NPD4511	Phase 1
0.7364	Intermediate Similarity	NPD8396	Approved
0.7364	Intermediate Similarity	NPD8395	Approved
0.7339	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD3875	Discontinued
0.7289	Intermediate Similarity	NPD1392	Approved
0.7285	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2175	Phase 3
0.7285	Intermediate Similarity	NPD2176	Approved
0.7285	Intermediate Similarity	NPD2177	Approved
0.7284	Intermediate Similarity	NPD5930	Phase 3
0.7273	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD8427	Approved
0.722	Intermediate Similarity	NPD8467	Approved
0.722	Intermediate Similarity	NPD8465	Approved
0.722	Intermediate Similarity	NPD8429	Approved
0.722	Intermediate Similarity	NPD8428	Approved
0.722	Intermediate Similarity	NPD8466	Approved
0.7212	Intermediate Similarity	NPD5429	Discontinued
0.7212	Intermediate Similarity	NPD6290	Phase 2
0.721	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3815	Phase 1
0.7205	Intermediate Similarity	NPD3816	Phase 1
0.7197	Intermediate Similarity	NPD3746	Discontinued
0.7197	Intermediate Similarity	NPD4885	Approved
0.7172	Intermediate Similarity	NPD6517	Phase 3
0.7163	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5066	Phase 2
0.7162	Intermediate Similarity	NPD5067	Phase 2
0.7143	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD1038	Approved
0.713	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5632	Approved
0.7117	Intermediate Similarity	NPD7948	Phase 1
0.711	Intermediate Similarity	NPD8426	Approved
0.711	Intermediate Similarity	NPD8425	Approved
0.711	Intermediate Similarity	NPD8459	Approved
0.711	Intermediate Similarity	NPD8460	Approved
0.7103	Intermediate Similarity	NPD8091	Phase 3
0.7093	Intermediate Similarity	NPD8403	Phase 1
0.7091	Intermediate Similarity	NPD3921	Approved
0.7091	Intermediate Similarity	NPD3924	Approved
0.7091	Intermediate Similarity	NPD3923	Approved
0.7091	Intermediate Similarity	NPD3922	Approved
0.7086	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1954	Phase 1
0.7076	Intermediate Similarity	NPD7221	Approved
0.7076	Intermediate Similarity	NPD7219	Approved
0.7068	Intermediate Similarity	NPD6243	Phase 3
0.7068	Intermediate Similarity	NPD6244	Phase 3
0.7051	Intermediate Similarity	NPD7395	Discontinued
0.7045	Intermediate Similarity	NPD6230	Discontinued
0.7045	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5913	Phase 3
0.7031	Intermediate Similarity	NPD6456	Discontinued
0.7027	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD7955	Approved
0.7008	Intermediate Similarity	NPD7956	Approved
0.7	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8358	Approved
0.6983	Remote Similarity	NPD4927	Discontinued
0.6982	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4083	Discontinued
0.6977	Remote Similarity	NPD7479	Phase 2
0.6969	Remote Similarity	NPD7169	Suspended
0.6967	Remote Similarity	NPD4454	Phase 2
0.6964	Remote Similarity	NPD6716	Phase 1
0.6958	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD6978	Phase 2
0.6957	Remote Similarity	NPD2916	Discontinued
0.6951	Remote Similarity	NPD6590	Discontinued
0.6936	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1325	Approved
0.6934	Remote Similarity	NPD1326	Approved
0.693	Remote Similarity	NPD6159	Phase 2
0.6906	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5479	Discontinued
0.6885	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7671	Approved
0.6883	Remote Similarity	NPD7672	Approved
0.688	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5488	Discontinued
0.6877	Remote Similarity	NPD7859	Phase 2
0.6873	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6873	Remote Similarity	NPD7803	Approved
0.6867	Remote Similarity	NPD6220	Phase 3
0.6862	Remote Similarity	NPD1856	Discontinued
0.6862	Remote Similarity	NPD6736	Discontinued
0.686	Remote Similarity	NPD7555	Discontinued
0.6857	Remote Similarity	NPD6964	Approved
0.6857	Remote Similarity	NPD6963	Approved
0.6849	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6530	Approved
0.6848	Remote Similarity	NPD6531	Approved
0.6846	Remote Similarity	NPD7603	Discontinued
0.6846	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7674	Phase 3
0.6846	Remote Similarity	NPD7675	Phase 3
0.6844	Remote Similarity	NPD5512	Phase 3
0.6842	Remote Similarity	NPD6750	Phase 2
0.6842	Remote Similarity	NPD7181	Phase 3
0.6835	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4795	Phase 2
0.6825	Remote Similarity	NPD8489	Phase 1
0.6824	Remote Similarity	NPD8442	Discontinued
0.6816	Remote Similarity	NPD4080	Discontinued
0.6815	Remote Similarity	NPD5905	Phase 1
0.6815	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8016	Phase 3
0.6814	Remote Similarity	NPD4605	Approved
0.6814	Remote Similarity	NPD5003	Discontinued
0.6814	Remote Similarity	NPD4604	Approved
0.6814	Remote Similarity	NPD6988	Phase 1
0.6812	Remote Similarity	NPD6975	Discontinued
0.6807	Remote Similarity	NPD6455	Phase 3
0.6805	Remote Similarity	NPD7719	Discontinued
0.6804	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1505	Phase 2
0.68	Remote Similarity	NPD4418	Discontinued
0.6797	Remote Similarity	NPD6150	Discontinued
0.6797	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5416	Discontinued
0.6795	Remote Similarity	NPD4131	Phase 3
0.6789	Remote Similarity	NPD2951	Discontinued
0.6787	Remote Similarity	NPD5256	Discontinued
0.6787	Remote Similarity	NPD7417	Discontinued
0.6781	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6550	Discontinued
0.6766	Remote Similarity	NPD3330	Phase 1
0.6762	Remote Similarity	NPD8512	Phase 3
0.676	Remote Similarity	NPD6473	Phase 1
0.6754	Remote Similarity	NPD3825	Phase 3
0.675	Remote Similarity	NPD7726	Phase 1
0.6747	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8284	Discontinued
0.6738	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4996	Approved
0.6735	Remote Similarity	NPD6962	Phase 2
0.6735	Remote Similarity	NPD4995	Approved
0.6733	Remote Similarity	NPD7068	Approved
0.6733	Remote Similarity	NPD7067	Approved
0.6732	Remote Similarity	NPD5482	Discontinued
0.6728	Remote Similarity	NPD4354	Approved
0.6726	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1740	Approved
0.6725	Remote Similarity	NPD1739	Approved
0.6721	Remote Similarity	NPD5559	Phase 2
0.6718	Remote Similarity	NPD7708	Approved
0.6713	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6569	Phase 2
0.6709	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7426	Phase 1
0.6696	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7069	Discontinued
0.6695	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4925	Approved
0.6694	Remote Similarity	NPD7853	Phase 2
0.6694	Remote Similarity	NPD7567	Approved
0.6682	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD802	Phase 2
0.6681	Remote Similarity	NPD4548	Discontinued
0.6681	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6742	Phase 2
0.668	Remote Similarity	NPD6743	Phase 2
0.668	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD3343	Phase 3
0.6667	Remote Similarity	NPD7592	Phase 2
0.6667	Remote Similarity	NPD7586	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