NPASS Compound

Structure

NPC473189 OpenBabel07101718272D 31 36 0 0 0 0 0 0 0 0999 V2000 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1576 -1.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7454 -0.6872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1631 -1.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3387 0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7564 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3442 0.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 0.8309 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 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7564 1.1399 0.0000 N 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 -0.9781 -0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 -1.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 20 2 0 0 0 0 7 21 2 0 0 0 0 8 24 2 0 0 0 0 9 26 2 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 31 1 0 0 0 0 17 19 1 0 0 0 0 17 31 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 23 1 0 0 0 0 21 26 1 0 0 0 0 22 25 2 0 0 0 0 23 27 2 0 0 0 0 24 28 1 0 0 0 0 25 28 1 0 0 0 0 26 29 1 0 0 0 0 27 29 1 0 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.17
Volume:	432.146
LogP:	6.203
LogD:	4.651
LogS:	-7.731
# Rotatable Bonds:	5
TPSA:	39.18
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	2.433
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:	-5.022
MDCK Permeability:	1.9639390302472748e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.247
Plasma Protein Binding (PPB):	99.3404769897461%
Volume Distribution (VD):	1.49
Pgp-substrate:	0.5748617649078369%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.714
CYP2C19-inhibitor:	0.911
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.966
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.386

ADMET: Excretion

Clearance (CL):	4.233
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.786
AMES Toxicity:	0.904
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.622
Carcinogencity:	0.906
Eye Corrosion:	0.003
Eye Irritation:	0.91
Respiratory Toxicity:	0.35

Download Data

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

Natural Product: NPC473189

Natural Product ID:	NPC473189
*Common Name:**	VGCTWZOPPKWZTP-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VGCTWZOPPKWZTP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H22N2O2/c1-30-29-26-9-5-3-7-21(26)23-15-19(11-13-27(23)29)17-31-16-18-10-12-25-22(14-18)20-6-2-4-8-24(20)28-25/h2-15,28H,16-17H2,1H3
SMILES:	COn1c2ccccc2c2c1ccc(c2)COCc1ccc2c(c1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633085
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
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21900.0	nM	PMID[535830]

☑ 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 NPC473189 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	605
0.1-0.2	3352
0.2-0.3	13832
0.3-0.4	15874
0.4-0.5	4907
0.5-0.6	2282
0.6-0.7	1512
0.7-0.8	323
0.8-0.85	6
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9573	High Similarity	NPC56618
0.9075	High Similarity	NPC473177
0.882	High Similarity	NPC473178
0.8238	Intermediate Similarity	NPC94157
0.8229	Intermediate Similarity	NPC199667
0.8177	Intermediate Similarity	NPC473181
0.8144	Intermediate Similarity	NPC473180
0.8077	Intermediate Similarity	NPC160381
0.804	Intermediate Similarity	NPC132642
0.8032	Intermediate Similarity	NPC72211
0.8	Intermediate Similarity	NPC477532
0.799	Intermediate Similarity	NPC473179
0.7968	Intermediate Similarity	NPC205934
0.7968	Intermediate Similarity	NPC195314
0.7968	Intermediate Similarity	NPC43787
0.795	Intermediate Similarity	NPC477533
0.7926	Intermediate Similarity	NPC70259
0.7906	Intermediate Similarity	NPC267423
0.7884	Intermediate Similarity	NPC70956
0.7884	Intermediate Similarity	NPC243834
0.7845	Intermediate Similarity	NPC6093
0.7835	Intermediate Similarity	NPC476106
0.7829	Intermediate Similarity	NPC16667
0.7824	Intermediate Similarity	NPC162484
0.7821	Intermediate Similarity	NPC34508
0.7812	Intermediate Similarity	NPC476044
0.7796	Intermediate Similarity	NPC242928
0.7784	Intermediate Similarity	NPC8104
0.7778	Intermediate Similarity	NPC131017
0.7772	Intermediate Similarity	NPC475112
0.7772	Intermediate Similarity	NPC190007
0.7772	Intermediate Similarity	NPC291535
0.7772	Intermediate Similarity	NPC475085
0.7767	Intermediate Similarity	NPC252251
0.7747	Intermediate Similarity	NPC88363
0.773	Intermediate Similarity	NPC94943
0.7718	Intermediate Similarity	NPC473185
0.7708	Intermediate Similarity	NPC128823
0.7708	Intermediate Similarity	NPC32200
0.7701	Intermediate Similarity	NPC34271
0.7701	Intermediate Similarity	NPC46413
0.7692	Intermediate Similarity	NPC477531
0.7692	Intermediate Similarity	NPC475253
0.765	Intermediate Similarity	NPC270009
0.7644	Intermediate Similarity	NPC209174
0.7641	Intermediate Similarity	NPC223427
0.764	Intermediate Similarity	NPC470508
0.7638	Intermediate Similarity	NPC208284
0.7626	Intermediate Similarity	NPC201697
0.7622	Intermediate Similarity	NPC176127
0.7622	Intermediate Similarity	NPC212535
0.7622	Intermediate Similarity	NPC473930
0.7616	Intermediate Similarity	NPC124005
0.7614	Intermediate Similarity	NPC67056
0.7611	Intermediate Similarity	NPC280548
0.7606	Intermediate Similarity	NPC246700
0.7602	Intermediate Similarity	NPC285558
0.76	Intermediate Similarity	NPC141353
0.76	Intermediate Similarity	NPC285469
0.7598	Intermediate Similarity	NPC86078
0.7596	Intermediate Similarity	NPC59269
0.7583	Intermediate Similarity	NPC39370
0.7581	Intermediate Similarity	NPC284678
0.7581	Intermediate Similarity	NPC84478
0.7577	Intermediate Similarity	NPC329747
0.7574	Intermediate Similarity	NPC170114
0.7571	Intermediate Similarity	NPC473186
0.7568	Intermediate Similarity	NPC192270
0.7568	Intermediate Similarity	NPC314394
0.7561	Intermediate Similarity	NPC179365
0.7561	Intermediate Similarity	NPC475450
0.7556	Intermediate Similarity	NPC154293
0.7554	Intermediate Similarity	NPC472443
0.7547	Intermediate Similarity	NPC473187
0.7543	Intermediate Similarity	NPC207726
0.7536	Intermediate Similarity	NPC473182
0.7527	Intermediate Similarity	NPC19679
0.7527	Intermediate Similarity	NPC472444
0.7525	Intermediate Similarity	NPC470549
0.7525	Intermediate Similarity	NPC193777
0.75	Intermediate Similarity	NPC126066
0.75	Intermediate Similarity	NPC211997
0.75	Intermediate Similarity	NPC473184
0.75	Intermediate Similarity	NPC193761
0.7487	Intermediate Similarity	NPC329793
0.7486	Intermediate Similarity	NPC329688
0.7486	Intermediate Similarity	NPC189812
0.7475	Intermediate Similarity	NPC45190
0.7474	Intermediate Similarity	NPC67288
0.7473	Intermediate Similarity	NPC474798
0.7472	Intermediate Similarity	NPC473320
0.7462	Intermediate Similarity	NPC477135
0.7459	Intermediate Similarity	NPC317430
0.7447	Intermediate Similarity	NPC15102
0.7446	Intermediate Similarity	NPC134586
0.7443	Intermediate Similarity	NPC38736
0.7439	Intermediate Similarity	NPC473587
0.7437	Intermediate Similarity	NPC249583
0.7433	Intermediate Similarity	NPC139291
0.7433	Intermediate Similarity	NPC472108
0.7432	Intermediate Similarity	NPC472123
0.743	Intermediate Similarity	NPC473183
0.7426	Intermediate Similarity	NPC294620
0.7426	Intermediate Similarity	NPC48353
0.7424	Intermediate Similarity	NPC470930
0.7423	Intermediate Similarity	NPC153042
0.7421	Intermediate Similarity	NPC128751
0.7419	Intermediate Similarity	NPC198339
0.7416	Intermediate Similarity	NPC227908
0.7416	Intermediate Similarity	NPC92796
0.7416	Intermediate Similarity	NPC202503
0.7416	Intermediate Similarity	NPC135141
0.7402	Intermediate Similarity	NPC36405
0.7401	Intermediate Similarity	NPC184476
0.74	Intermediate Similarity	NPC475910
0.74	Intermediate Similarity	NPC314957
0.7399	Intermediate Similarity	NPC129042
0.7396	Intermediate Similarity	NPC55493
0.7394	Intermediate Similarity	NPC165201
0.7394	Intermediate Similarity	NPC475428
0.7391	Intermediate Similarity	NPC472586
0.7389	Intermediate Similarity	NPC31700
0.7387	Intermediate Similarity	NPC300156
0.7384	Intermediate Similarity	NPC242556
0.7382	Intermediate Similarity	NPC469497
0.7382	Intermediate Similarity	NPC106833
0.7378	Intermediate Similarity	NPC473762
0.7368	Intermediate Similarity	NPC98371
0.7368	Intermediate Similarity	NPC313884
0.7363	Intermediate Similarity	NPC63751
0.7354	Intermediate Similarity	NPC476319
0.7353	Intermediate Similarity	NPC312092
0.735	Intermediate Similarity	NPC4687
0.7337	Intermediate Similarity	NPC97525
0.7337	Intermediate Similarity	NPC474409
0.7327	Intermediate Similarity	NPC167860
0.7327	Intermediate Similarity	NPC471304
0.7327	Intermediate Similarity	NPC123976
0.7313	Intermediate Similarity	NPC39679
0.7312	Intermediate Similarity	NPC293472
0.731	Intermediate Similarity	NPC11017
0.7308	Intermediate Similarity	NPC198503
0.7304	Intermediate Similarity	NPC469592
0.7304	Intermediate Similarity	NPC471080
0.7302	Intermediate Similarity	NPC472294
0.7293	Intermediate Similarity	NPC311276
0.7292	Intermediate Similarity	NPC76748
0.7292	Intermediate Similarity	NPC329858
0.7292	Intermediate Similarity	NPC95783
0.729	Intermediate Similarity	NPC180504
0.7283	Intermediate Similarity	NPC126492
0.7282	Intermediate Similarity	NPC231342
0.7282	Intermediate Similarity	NPC205403
0.7277	Intermediate Similarity	NPC119700
0.7273	Intermediate Similarity	NPC72980
0.7273	Intermediate Similarity	NPC53947
0.7268	Intermediate Similarity	NPC475190
0.7268	Intermediate Similarity	NPC307963
0.7264	Intermediate Similarity	NPC477065
0.7259	Intermediate Similarity	NPC74413
0.7258	Intermediate Similarity	NPC84347
0.7258	Intermediate Similarity	NPC288785
0.7256	Intermediate Similarity	NPC277351
0.7256	Intermediate Similarity	NPC250361
0.7255	Intermediate Similarity	NPC308137
0.7255	Intermediate Similarity	NPC310211
0.7254	Intermediate Similarity	NPC92111
0.7247	Intermediate Similarity	NPC471458
0.7247	Intermediate Similarity	NPC470507
0.7245	Intermediate Similarity	NPC232130
0.7241	Intermediate Similarity	NPC475422
0.7241	Intermediate Similarity	NPC475165
0.724	Intermediate Similarity	NPC111602
0.724	Intermediate Similarity	NPC102338
0.724	Intermediate Similarity	NPC63199
0.724	Intermediate Similarity	NPC296527
0.724	Intermediate Similarity	NPC196251
0.7236	Intermediate Similarity	NPC260900
0.7236	Intermediate Similarity	NPC123019
0.7231	Intermediate Similarity	NPC181502
0.7231	Intermediate Similarity	NPC85066
0.7225	Intermediate Similarity	NPC280799
0.7222	Intermediate Similarity	NPC176538
0.7222	Intermediate Similarity	NPC214428
0.7222	Intermediate Similarity	NPC249040
0.7222	Intermediate Similarity	NPC475151
0.7222	Intermediate Similarity	NPC230869
0.722	Intermediate Similarity	NPC478074
0.7216	Intermediate Similarity	NPC187951
0.7216	Intermediate Similarity	NPC37548
0.7213	Intermediate Similarity	NPC49954
0.7213	Intermediate Similarity	NPC474561
0.7206	Intermediate Similarity	NPC87413
0.7206	Intermediate Similarity	NPC187501
0.7206	Intermediate Similarity	NPC250129
0.7202	Intermediate Similarity	NPC469501
0.7202	Intermediate Similarity	NPC469470
0.72	Intermediate Similarity	NPC288838
0.7198	Intermediate Similarity	NPC194640
0.7198	Intermediate Similarity	NPC476118

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 NPC473189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	702
0.2-0.3	824
0.3-0.4	1650
0.4-0.5	2955
0.5-0.6	2024
0.6-0.7	565
0.7-0.8	60
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
0.8297	Intermediate Similarity	NPD5913	Phase 3
0.8297	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD1326	Approved
0.8114	Intermediate Similarity	NPD1325	Approved
0.7802	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5003	Discontinued
0.773	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3835	Phase 3
0.7674	Intermediate Similarity	NPD3833	Phase 3
0.7617	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD8395	Approved
0.7617	Intermediate Similarity	NPD8396	Approved
0.7609	Intermediate Similarity	NPD6595	Phase 3
0.7572	Intermediate Similarity	NPD4462	Approved
0.7572	Intermediate Similarity	NPD4463	Approved
0.7566	Intermediate Similarity	NPD2564	Approved
0.7566	Intermediate Similarity	NPD2565	Phase 2
0.7563	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6158	Phase 2
0.75	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD8403	Phase 1
0.746	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD8431	Approved
0.744	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6995	Phase 1
0.7405	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5065	Approved
0.7387	Intermediate Similarity	NPD3003	Approved
0.7382	Intermediate Similarity	NPD6281	Approved
0.7376	Intermediate Similarity	NPD7470	Discontinued
0.7368	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1592	Phase 3
0.7366	Intermediate Similarity	NPD8386	Phase 2
0.7363	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5903	Approved
0.7353	Intermediate Similarity	NPD5902	Approved
0.7313	Intermediate Similarity	NPD5658	Approved
0.7312	Intermediate Similarity	NPD2144	Approved
0.7299	Intermediate Similarity	NPD6978	Phase 2
0.7299	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD1038	Approved
0.7268	Intermediate Similarity	NPD2844	Phase 3
0.7268	Intermediate Similarity	NPD5021	Discontinued
0.725	Intermediate Similarity	NPD5901	Discontinued
0.7245	Intermediate Similarity	NPD7948	Phase 1
0.7232	Intermediate Similarity	NPD2882	Phase 1
0.7231	Intermediate Similarity	NPD6251	Discontinued
0.7231	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6492	Phase 2
0.72	Intermediate Similarity	NPD4886	Phase 2
0.72	Intermediate Similarity	NPD2920	Discontinued
0.7198	Intermediate Similarity	NPD5140	Approved
0.7198	Intermediate Similarity	NPD5138	Approved
0.7196	Intermediate Similarity	NPD3038	Discontinued
0.7196	Intermediate Similarity	NPD7688	Phase 1
0.7192	Intermediate Similarity	NPD4506	Discontinued
0.7184	Intermediate Similarity	NPD5254	Discontinued
0.7178	Intermediate Similarity	NPD7222	Phase 2
0.7175	Intermediate Similarity	NPD2172	Phase 1
0.7174	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6227	Discontinued
0.7172	Intermediate Similarity	NPD3825	Phase 3
0.7164	Intermediate Similarity	NPD5426	Phase 3
0.7158	Intermediate Similarity	NPD5596	Phase 2
0.715	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2509	Approved
0.7143	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2510	Approved
0.7129	Intermediate Similarity	NPD6455	Phase 3
0.7129	Intermediate Similarity	NPD7194	Discontinued
0.7128	Intermediate Similarity	NPD3404	Approved
0.7113	Intermediate Similarity	NPD4499	Approved
0.711	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4511	Phase 1
0.7095	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7453	Approved
0.7094	Intermediate Similarity	NPD7452	Approved
0.7092	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3330	Phase 1
0.7085	Intermediate Similarity	NPD1768	Approved
0.7081	Intermediate Similarity	NPD6985	Discontinued
0.7074	Intermediate Similarity	NPD2381	Approved
0.7074	Intermediate Similarity	NPD2380	Approved
0.7074	Intermediate Similarity	NPD2382	Approved
0.7059	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6452	Discontinued
0.7048	Intermediate Similarity	NPD3402	Phase 1
0.7048	Intermediate Similarity	NPD6770	Approved
0.7044	Intermediate Similarity	NPD6150	Discontinued
0.7035	Intermediate Similarity	NPD7946	Pre-registration
0.7022	Intermediate Similarity	NPD3100	Discontinued
0.702	Intermediate Similarity	NPD6550	Discontinued
0.7018	Intermediate Similarity	NPD4880	Discontinued
0.7016	Intermediate Similarity	NPD4203	Approved
0.7016	Intermediate Similarity	NPD4204	Approved
0.7	Intermediate Similarity	NPD4076	Approved
0.7	Intermediate Similarity	NPD4079	Approved
0.699	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5612	Discontinued
0.698	Remote Similarity	NPD5023	Discontinued
0.6973	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7558	Phase 2
0.6971	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4418	Discontinued
0.6965	Remote Similarity	NPD4600	Approved
0.6965	Remote Similarity	NPD4500	Approved
0.6965	Remote Similarity	NPD4501	Approved
0.6965	Remote Similarity	NPD4601	Approved
0.6961	Remote Similarity	NPD7957	Phase 1
0.6961	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5067	Phase 2
0.6957	Remote Similarity	NPD5066	Phase 2
0.6957	Remote Similarity	NPD6220	Phase 3
0.6947	Remote Similarity	NPD3506	Approved
0.6947	Remote Similarity	NPD6159	Phase 2
0.6947	Remote Similarity	NPD3505	Approved
0.6946	Remote Similarity	NPD6176	Phase 1
0.6946	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1262	Discovery
0.6935	Remote Similarity	NPD2642	Approved
0.6935	Remote Similarity	NPD2639	Approved
0.6927	Remote Similarity	NPD7867	Phase 1
0.6923	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8093	Discontinued
0.6919	Remote Similarity	NPD3323	Discontinued
0.6911	Remote Similarity	NPD3920	Phase 2
0.691	Remote Similarity	NPD1683	Approved
0.69	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6208	Discontinued
0.6895	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7671	Approved
0.6893	Remote Similarity	NPD7672	Approved
0.689	Remote Similarity	NPD8094	Discontinued
0.6885	Remote Similarity	NPD2581	Approved
0.6885	Remote Similarity	NPD2582	Approved
0.6884	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5530	Phase 1
0.6872	Remote Similarity	NPD5256	Discontinued
0.6872	Remote Similarity	NPD5164	Discontinued
0.6866	Remote Similarity	NPD5559	Phase 2
0.6866	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD8358	Approved
0.6857	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6242	Discontinued
0.685	Remote Similarity	NPD7935	Phase 2
0.6849	Remote Similarity	NPD4885	Approved
0.6848	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1392	Approved
0.684	Remote Similarity	NPD5632	Approved
0.6837	Remote Similarity	NPD4948	Discontinued
0.6836	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6969	Phase 2
0.6835	Remote Similarity	NPD6968	Phase 2
0.6834	Remote Similarity	NPD802	Phase 2
0.6833	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.683	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3947	Discontinued
0.6825	Remote Similarity	NPD3393	Approved
0.6825	Remote Similarity	NPD3389	Approved
0.6825	Remote Similarity	NPD3394	Approved
0.6818	Remote Similarity	NPD7709	Discontinued
0.6816	Remote Similarity	NPD7081	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2189	Approved
0.6812	Remote Similarity	NPD2187	Approved
0.6811	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD3875	Discontinued
0.6804	Remote Similarity	NPD5106	Approved
0.6804	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5105	Approved
0.6802	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6590	Discontinued
0.68	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7001	Phase 3
0.6796	Remote Similarity	NPD7010	Phase 3
0.6792	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7418	Discontinued
0.6782	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6991	Approved
0.6777	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1685	Approved
0.6774	Remote Similarity	NPD1684	Approved
0.6769	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8063	Discontinued
0.6765	Remote Similarity	NPD6145	Phase 1
0.6763	Remote Similarity	NPD3385	Approved
0.6763	Remote Similarity	NPD5429	Discontinued
0.6761	Remote Similarity	NPD786	Approved
0.6751	Remote Similarity	NPD2383	Phase 1

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