NPASS Compound

Structure

NPC473179 OpenBabel07101718242D 31 36 0 0 0 0 0 0 0 0999 V2000 -5.2812 1.1910 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 -8.4727 -2.6826 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 -8.0659 -3.5962 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 -7.8849 -1.8736 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 -7.0714 -3.7007 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 -6.1472 -0.3090 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 -3.5491 -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 -5.2812 0.1910 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 -6.8904 -1.9781 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 -6.1472 -1.3090 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 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 -2.8917 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 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 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 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4891 -2.7872 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 -3.5491 0.1910 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 15 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 17 2 0 0 0 0 8 18 2 0 0 0 0 9 22 2 0 0 0 0 10 23 2 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 24 2 0 0 0 0 15 27 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 21 25 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 26 1 0 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.17
Volume:	432.146
LogP:	6.296
LogD:	4.397
LogS:	-4.812
# Rotatable Bonds:	3
TPSA:	61.04
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	2.562
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:	-5.851
MDCK Permeability:	8.463813173875678e-06
Pgp-inhibitor:	0.952
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.725
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	98.9044418334961%
Volume Distribution (VD):	0.934
Pgp-substrate:	1.576219916343689%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.722
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.764
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.379
CYP3A4-substrate:	0.676

ADMET: Excretion

Clearance (CL):	4.971
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.848
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.919
Carcinogencity:	0.813
Eye Corrosion:	0.003
Eye Irritation:	0.82
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC473179

Natural Product ID:	NPC473179
*Common Name:**	JXLLFTIVHZYBIO-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JXLLFTIVHZYBIO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H22N2O2/c1-15-11-19-17-7-3-5-9-22(17)28-25(19)21(27(15)30)13-16-12-20-18-8-4-6-10-23(18)29-26(20)24(14-16)31-2/h3-12,14,28-30H,13H2,1-2H3
SMILES:	COc1cc(cc2c1[nH]c1c2cccc1)Cc1c(O)c(C)cc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633075
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[551841]

☑ 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 NPC473179 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	668
0.1-0.2	4110
0.2-0.3	13316
0.3-0.4	5706
0.4-0.5	13944
0.5-0.6	3099
0.6-0.7	1402
0.7-0.8	371
0.8-0.85	47
0.85-0.9	22
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9652	High Similarity	NPC473185
0.9417	High Similarity	NPC473182
0.9282	High Similarity	NPC473183
0.9279	High Similarity	NPC473184
0.922	High Similarity	NPC202503
0.9192	High Similarity	NPC199667
0.9141	High Similarity	NPC473181
0.91	High Similarity	NPC473180
0.9069	High Similarity	NPC132642
0.9043	High Similarity	NPC475253
0.9005	High Similarity	NPC94157
0.8969	High Similarity	NPC243834
0.8969	High Similarity	NPC70956
0.895	High Similarity	NPC209769
0.8932	High Similarity	NPC477532
0.8857	High Similarity	NPC252251
0.8844	High Similarity	NPC470930
0.8782	High Similarity	NPC128823
0.8774	High Similarity	NPC477531
0.8756	High Similarity	NPC193777
0.8744	High Similarity	NPC475085
0.8744	High Similarity	NPC291535
0.8744	High Similarity	NPC475112
0.8726	High Similarity	NPC209174
0.8608	High Similarity	NPC242928
0.8579	High Similarity	NPC131017
0.8544	High Similarity	NPC48353
0.8543	High Similarity	NPC72211
0.8522	High Similarity	NPC476106
0.8515	High Similarity	NPC162484
0.8482	Intermediate Similarity	NPC473188
0.8454	Intermediate Similarity	NPC94943
0.8442	Intermediate Similarity	NPC70259
0.844	Intermediate Similarity	NPC473187
0.8436	Intermediate Similarity	NPC477533
0.8416	Intermediate Similarity	NPC267423
0.8402	Intermediate Similarity	NPC190007
0.8392	Intermediate Similarity	NPC43787
0.8392	Intermediate Similarity	NPC205934
0.8364	Intermediate Similarity	NPC179287
0.8351	Intermediate Similarity	NPC212535
0.8333	Intermediate Similarity	NPC223427
0.8311	Intermediate Similarity	NPC277351
0.8309	Intermediate Similarity	NPC201697
0.8308	Intermediate Similarity	NPC153042
0.8299	Intermediate Similarity	NPC474798
0.8235	Intermediate Similarity	NPC476044
0.8227	Intermediate Similarity	NPC39370
0.8227	Intermediate Similarity	NPC18487
0.8219	Intermediate Similarity	NPC473186
0.8216	Intermediate Similarity	NPC208084
0.8195	Intermediate Similarity	NPC135887
0.8195	Intermediate Similarity	NPC199277
0.8173	Intermediate Similarity	NPC470931
0.816	Intermediate Similarity	NPC170114
0.8155	Intermediate Similarity	NPC475774
0.8152	Intermediate Similarity	NPC469592
0.8152	Intermediate Similarity	NPC471080
0.8113	Intermediate Similarity	NPC470549
0.8093	Intermediate Similarity	NPC86078
0.8093	Intermediate Similarity	NPC150239
0.8084	Intermediate Similarity	NPC184408
0.803	Intermediate Similarity	NPC84478
0.8029	Intermediate Similarity	NPC285558
0.801	Intermediate Similarity	NPC329747
0.8009	Intermediate Similarity	NPC11464
0.8	Intermediate Similarity	NPC274640
0.8	Intermediate Similarity	NPC247803
0.8	Intermediate Similarity	NPC475910
0.8	Intermediate Similarity	NPC469594
0.799	Intermediate Similarity	NPC473189
0.798	Intermediate Similarity	NPC475190
0.7973	Intermediate Similarity	NPC469554
0.7972	Intermediate Similarity	NPC87413
0.7963	Intermediate Similarity	NPC193267
0.7963	Intermediate Similarity	NPC213530
0.796	Intermediate Similarity	NPC246700
0.7936	Intermediate Similarity	NPC144452
0.7934	Intermediate Similarity	NPC294620
0.7931	Intermediate Similarity	NPC114335
0.7931	Intermediate Similarity	NPC280964
0.7931	Intermediate Similarity	NPC141915
0.7926	Intermediate Similarity	NPC225279
0.7919	Intermediate Similarity	NPC88363
0.7915	Intermediate Similarity	NPC89549
0.7909	Intermediate Similarity	NPC200888
0.7909	Intermediate Similarity	NPC227908
0.79	Intermediate Similarity	NPC51388
0.7897	Intermediate Similarity	NPC474409
0.7897	Intermediate Similarity	NPC39500
0.7892	Intermediate Similarity	NPC101543
0.7887	Intermediate Similarity	NPC187501
0.787	Intermediate Similarity	NPC314552
0.786	Intermediate Similarity	NPC118228
0.7844	Intermediate Similarity	NPC174760
0.7837	Intermediate Similarity	NPC11017
0.7834	Intermediate Similarity	NPC303658
0.783	Intermediate Similarity	NPC39679
0.7828	Intermediate Similarity	NPC72980
0.7824	Intermediate Similarity	NPC8022
0.7824	Intermediate Similarity	NPC470799
0.7814	Intermediate Similarity	NPC478074
0.7811	Intermediate Similarity	NPC42591
0.7797	Intermediate Similarity	NPC11408
0.7783	Intermediate Similarity	NPC4687
0.7783	Intermediate Similarity	NPC128751
0.7783	Intermediate Similarity	NPC249583
0.7773	Intermediate Similarity	NPC164374
0.7773	Intermediate Similarity	NPC137929
0.7768	Intermediate Similarity	NPC474688
0.7767	Intermediate Similarity	NPC310211
0.7767	Intermediate Similarity	NPC308137
0.7757	Intermediate Similarity	NPC167860
0.7757	Intermediate Similarity	NPC123976
0.7753	Intermediate Similarity	NPC6786
0.7752	Intermediate Similarity	NPC46561
0.7745	Intermediate Similarity	NPC106833
0.7745	Intermediate Similarity	NPC469497
0.7742	Intermediate Similarity	NPC3207
0.7742	Intermediate Similarity	NPC183407
0.7738	Intermediate Similarity	NPC211416
0.7729	Intermediate Similarity	NPC475844
0.7729	Intermediate Similarity	NPC217554
0.7727	Intermediate Similarity	NPC198503
0.7725	Intermediate Similarity	NPC476138
0.7725	Intermediate Similarity	NPC245816
0.7721	Intermediate Similarity	NPC208284
0.7721	Intermediate Similarity	NPC23294
0.7711	Intermediate Similarity	NPC176127
0.771	Intermediate Similarity	NPC469589
0.7706	Intermediate Similarity	NPC293151
0.7706	Intermediate Similarity	NPC169402
0.77	Intermediate Similarity	NPC478032
0.7696	Intermediate Similarity	NPC116238
0.7689	Intermediate Similarity	NPC474701
0.7686	Intermediate Similarity	NPC477861
0.7685	Intermediate Similarity	NPC316981
0.7685	Intermediate Similarity	NPC26679
0.7679	Intermediate Similarity	NPC314954
0.7678	Intermediate Similarity	NPC66815
0.7674	Intermediate Similarity	NPC303951
0.765	Intermediate Similarity	NPC266931
0.7638	Intermediate Similarity	NPC56618
0.763	Intermediate Similarity	NPC232727
0.7629	Intermediate Similarity	NPC284141
0.7628	Intermediate Similarity	NPC185782
0.7617	Intermediate Similarity	NPC283117
0.7613	Intermediate Similarity	NPC280272
0.7597	Intermediate Similarity	NPC475666
0.7583	Intermediate Similarity	NPC329793
0.7581	Intermediate Similarity	NPC210828
0.7581	Intermediate Similarity	NPC86834
0.757	Intermediate Similarity	NPC304183
0.7568	Intermediate Similarity	NPC310118
0.7558	Intermediate Similarity	NPC294375
0.7554	Intermediate Similarity	NPC208522
0.7554	Intermediate Similarity	NPC81939
0.7548	Intermediate Similarity	NPC307963
0.7545	Intermediate Similarity	NPC305984
0.7544	Intermediate Similarity	NPC180504
0.7522	Intermediate Similarity	NPC194740
0.7521	Intermediate Similarity	NPC132385
0.7512	Intermediate Similarity	NPC5145
0.7511	Intermediate Similarity	NPC473041
0.75	Intermediate Similarity	NPC19872
0.75	Intermediate Similarity	NPC118511
0.75	Intermediate Similarity	NPC99666
0.7488	Intermediate Similarity	NPC45190
0.7488	Intermediate Similarity	NPC300156
0.7476	Intermediate Similarity	NPC251090
0.7476	Intermediate Similarity	NPC46580
0.7476	Intermediate Similarity	NPC13880
0.7455	Intermediate Similarity	NPC162748
0.7453	Intermediate Similarity	NPC476167
0.7446	Intermediate Similarity	NPC184680
0.7431	Intermediate Similarity	NPC471304
0.7427	Intermediate Similarity	NPC314573
0.7425	Intermediate Similarity	NPC477066
0.7421	Intermediate Similarity	NPC330009
0.7419	Intermediate Similarity	NPC477111
0.7418	Intermediate Similarity	NPC249040
0.7415	Intermediate Similarity	NPC62069
0.7414	Intermediate Similarity	NPC470785
0.7414	Intermediate Similarity	NPC131486
0.7414	Intermediate Similarity	NPC470784
0.7411	Intermediate Similarity	NPC280799
0.7409	Intermediate Similarity	NPC476287
0.7406	Intermediate Similarity	NPC192315
0.7406	Intermediate Similarity	NPC306376
0.7404	Intermediate Similarity	NPC76748
0.7403	Intermediate Similarity	NPC295228
0.7401	Intermediate Similarity	NPC110151
0.7397	Intermediate Similarity	NPC9894
0.7395	Intermediate Similarity	NPC133609
0.7393	Intermediate Similarity	NPC478081
0.7368	Intermediate Similarity	NPC92111
0.7364	Intermediate Similarity	NPC203168
0.7364	Intermediate Similarity	NPC189079
0.7361	Intermediate Similarity	NPC470500
0.7356	Intermediate Similarity	NPC296527

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 NPC473179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	716
0.2-0.3	889
0.3-0.4	1682
0.4-0.5	2909
0.5-0.6	1845
0.6-0.7	617
0.7-0.8	95
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8028	Intermediate Similarity	NPD5902	Approved
0.8028	Intermediate Similarity	NPD5903	Approved
0.799	Intermediate Similarity	NPD3003	Approved
0.7952	Intermediate Similarity	NPD7222	Phase 2
0.7936	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7915	Intermediate Similarity	NPD5658	Approved
0.787	Intermediate Similarity	NPD5164	Discontinued
0.7867	Intermediate Similarity	NPD7452	Approved
0.7867	Intermediate Similarity	NPD7453	Approved
0.7857	Intermediate Similarity	NPD7558	Phase 2
0.7804	Intermediate Similarity	NPD4502	Phase 2
0.7788	Intermediate Similarity	NPD8396	Approved
0.7788	Intermediate Similarity	NPD8395	Approved
0.7768	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD6985	Discontinued
0.7717	Intermediate Similarity	NPD3875	Discontinued
0.7717	Intermediate Similarity	NPD7194	Discontinued
0.7703	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1768	Approved
0.7661	Intermediate Similarity	NPD5612	Discontinued
0.7586	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5530	Phase 1
0.7563	Intermediate Similarity	NPD8244	Phase 2
0.7549	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1038	Approved
0.7541	Intermediate Similarity	NPD8364	Approved
0.7541	Intermediate Similarity	NPD8363	Approved
0.7534	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7948	Phase 1
0.7488	Intermediate Similarity	NPD8403	Phase 1
0.748	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5936	Approved
0.7477	Intermediate Similarity	NPD5939	Approved
0.7467	Intermediate Similarity	NPD6494	Phase 2
0.7465	Intermediate Similarity	NPD4511	Phase 1
0.7454	Intermediate Similarity	NPD1392	Approved
0.7454	Intermediate Similarity	NPD5429	Discontinued
0.7452	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5913	Phase 3
0.7444	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2176	Approved
0.7371	Intermediate Similarity	NPD2175	Phase 3
0.7371	Intermediate Similarity	NPD2177	Approved
0.7354	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD5632	Approved
0.7346	Intermediate Similarity	NPD6590	Discontinued
0.734	Intermediate Similarity	NPD6159	Phase 2
0.7318	Intermediate Similarity	NPD5066	Phase 2
0.7318	Intermediate Similarity	NPD5067	Phase 2
0.7309	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7219	Approved
0.7301	Intermediate Similarity	NPD7221	Approved
0.7299	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6290	Phase 2
0.7291	Intermediate Similarity	NPD8427	Approved
0.7291	Intermediate Similarity	NPD8466	Approved
0.7291	Intermediate Similarity	NPD8428	Approved
0.7291	Intermediate Similarity	NPD8465	Approved
0.7291	Intermediate Similarity	NPD8429	Approved
0.7291	Intermediate Similarity	NPD8467	Approved
0.7277	Intermediate Similarity	NPD7395	Discontinued
0.7273	Intermediate Similarity	NPD3746	Discontinued
0.7264	Intermediate Similarity	NPD1326	Approved
0.7264	Intermediate Similarity	NPD1325	Approved
0.724	Intermediate Similarity	NPD6220	Phase 3
0.723	Intermediate Similarity	NPD5512	Phase 3
0.7225	Intermediate Similarity	NPD6736	Discontinued
0.722	Intermediate Similarity	NPD7479	Phase 2
0.722	Intermediate Similarity	NPD3920	Phase 2
0.7217	Intermediate Similarity	NPD7555	Discontinued
0.7205	Intermediate Similarity	NPD7603	Discontinued
0.7197	Intermediate Similarity	NPD8358	Approved
0.7196	Intermediate Similarity	NPD6988	Phase 1
0.7196	Intermediate Similarity	NPD5003	Discontinued
0.7183	Intermediate Similarity	NPD4418	Discontinued
0.7182	Intermediate Similarity	NPD2916	Discontinued
0.7177	Intermediate Similarity	NPD5256	Discontinued
0.7176	Intermediate Similarity	NPD8460	Approved
0.7176	Intermediate Similarity	NPD8425	Approved
0.7176	Intermediate Similarity	NPD8426	Approved
0.7176	Intermediate Similarity	NPD8459	Approved
0.7169	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5416	Discontinued
0.715	Intermediate Similarity	NPD6550	Discontinued
0.713	Intermediate Similarity	NPD3825	Phase 3
0.713	Intermediate Similarity	NPD3330	Phase 1
0.7124	Intermediate Similarity	NPD4885	Approved
0.7122	Intermediate Similarity	NPD4354	Approved
0.7112	Intermediate Similarity	NPD5479	Discontinued
0.7106	Intermediate Similarity	NPD4454	Phase 2
0.7104	Intermediate Similarity	NPD7672	Approved
0.7104	Intermediate Similarity	NPD7671	Approved
0.7101	Intermediate Similarity	NPD6473	Phase 1
0.7094	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3763	Approved
0.7089	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6569	Phase 2
0.7071	Intermediate Similarity	NPD7068	Approved
0.7071	Intermediate Similarity	NPD7067	Approved
0.707	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5559	Phase 2
0.7068	Intermediate Similarity	NPD8284	Discontinued
0.7067	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5482	Discontinued
0.7061	Intermediate Similarity	NPD5930	Phase 3
0.7056	Intermediate Similarity	NPD802	Phase 2
0.7048	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4795	Phase 2
0.7034	Intermediate Similarity	NPD7853	Phase 2
0.7033	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3402	Phase 1
0.7014	Intermediate Similarity	NPD6150	Discontinued
0.7009	Intermediate Similarity	NPD1505	Phase 2
0.7008	Intermediate Similarity	NPD6742	Phase 2
0.7008	Intermediate Similarity	NPD6743	Phase 2
0.7	Intermediate Similarity	NPD6991	Approved
0.7	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1954	Phase 1
0.6996	Remote Similarity	NPD6243	Phase 3
0.6996	Remote Similarity	NPD6244	Phase 3
0.6995	Remote Similarity	NPD2564	Approved
0.6995	Remote Similarity	NPD2565	Phase 2
0.6992	Remote Similarity	NPD2951	Discontinued
0.6987	Remote Similarity	NPD7417	Discontinued
0.6987	Remote Similarity	NPD6242	Discontinued
0.6986	Remote Similarity	NPD4204	Approved
0.6986	Remote Similarity	NPD4203	Approved
0.6981	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3816	Phase 1
0.6978	Remote Similarity	NPD3815	Phase 1
0.6972	Remote Similarity	NPD3814	Phase 1
0.6972	Remote Similarity	NPD4442	Phase 2
0.6971	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.696	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7726	Phase 1
0.6954	Remote Similarity	NPD3835	Phase 3
0.6954	Remote Similarity	NPD3833	Phase 3
0.6951	Remote Similarity	NPD2189	Approved
0.6951	Remote Similarity	NPD2187	Approved
0.6944	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5488	Discontinued
0.6941	Remote Similarity	NPD1739	Approved
0.6941	Remote Similarity	NPD1740	Approved
0.694	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6246	Approved
0.6927	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD3986	Discontinued
0.6926	Remote Similarity	NPD1856	Discontinued
0.6913	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4927	Discontinued
0.6903	Remote Similarity	NPD7069	Discontinued
0.6903	Remote Similarity	NPD6202	Discontinued
0.6901	Remote Similarity	NPD4350	Approved
0.6901	Remote Similarity	NPD4349	Approved
0.69	Remote Similarity	NPD4429	Discontinued
0.6895	Remote Similarity	NPD8091	Phase 3
0.6895	Remote Similarity	NPD5999	Phase 2
0.6895	Remote Similarity	NPD4548	Discontinued
0.6895	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7567	Approved
0.6892	Remote Similarity	NPD4038	Approved
0.6892	Remote Similarity	NPD32	Approved
0.6892	Remote Similarity	NPD4033	Approved
0.6892	Remote Similarity	NPD4034	Approved
0.6892	Remote Similarity	NPD4035	Approved
0.6892	Remote Similarity	NPD4037	Approved
0.6892	Remote Similarity	NPD4036	Approved
0.6892	Remote Similarity	NPD6456	Discontinued
0.6892	Remote Similarity	NPD31	Approved
0.6892	Remote Similarity	NPD4122	Approved
0.6892	Remote Similarity	NPD4039	Approved
0.6891	Remote Similarity	NPD3006	Discontinued
0.6888	Remote Similarity	NPD6716	Phase 1
0.6888	Remote Similarity	NPD6517	Phase 3
0.6886	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8489	Phase 1
0.688	Remote Similarity	NPD6978	Phase 2
0.6878	Remote Similarity	NPD6975	Discontinued
0.6878	Remote Similarity	NPD6208	Discontinued
0.6875	Remote Similarity	NPD8016	Phase 3
0.6875	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7955	Approved
0.6867	Remote Similarity	NPD7956	Approved
0.6866	Remote Similarity	NPD6251	Discontinued

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