NPASS Compound

Structure

NPC472293 OpenBabel07101718202D 27 30 0 0 1 0 0 0 0 0999 V2000 1.3071 -1.0304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1123 2.0240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3436 3.0658 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 -1.9890 1.8271 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 -1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6582 2.0161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6582 -0.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9414 0.7192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2777 -0.7896 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 3.3653 0.3090 0.0000 C 0 0 2 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 2.5546 0.1713 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 2.6582 2.0161 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6582 -0.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3653 1.3090 0.0000 C 0 0 1 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 4.2891 1.6917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9875 1.5403 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9715 -1.5099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2755 -1.3220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0825 1.0829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4197 2.6831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 23 1 0 0 0 0 3 27 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 12 2 0 0 0 0 7 16 2 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 24 2 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 9 1 6 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 16 22 1 0 0 0 0 17 8 1 1 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 25 2 0 0 0 0 19 21 1 1 0 0 0 20 22 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.16
Volume:	373.609
LogP:	2.254
LogD:	1.855
LogS:	-3.078
# Rotatable Bonds:	3
TPSA:	79.47
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.826
Synthetic Accessibility Score:	4.666
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.818
MDCK Permeability:	4.006310336990282e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.459
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	51.88996505737305%
Volume Distribution (VD):	1.557
Pgp-substrate:	59.323143005371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.584
CYP2C19-inhibitor:	0.655
CYP2C19-substrate:	0.366
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.743
CYP3A4-inhibitor:	0.555
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	6.845
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.774
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.567
Carcinogencity:	0.799
Eye Corrosion:	0.017
Eye Irritation:	0.114
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC472293

Natural Product ID:	NPC472293
*Common Name:**	XUMIPNQUXRLEBO-FMEYXAORSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUMIPNQUXRLEBO-FMEYXAORSA-N
Standard InCHI:	InChI=1S/C21H22N2O4/c1-11(24)15-10-23(2)17-8-14-12-6-4-5-7-16(12)22-20(14)18(25)9-13(15)19(17)21(26)27-3/h4-7,10,13,17,19,22H,8-9H2,1-3H3/t13-,17+,19+/m1/s1
SMILES:	CC(=O)C1=CN(C2CC3=C(C(=O)CC1C2C(=O)OC)NC4=CC=CC=C34)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358046
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002744] Vobasan alkaloids

*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
NPO32666	tabernaemontana	Genus	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333996]

☑ 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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[481396]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[481396]

☑ 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 NPC472293 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	313
0.1-0.2	2176
0.2-0.3	12309
0.3-0.4	18537
0.4-0.5	4837
0.5-0.6	2262
0.6-0.7	1812
0.7-0.8	431
0.8-0.85	11
0.85-0.9	0
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.983	High Similarity	NPC472297
0.983	High Similarity	NPC472296
0.9827	High Similarity	NPC472292
0.9435	High Similarity	NPC472210
0.9435	High Similarity	NPC247735
0.9435	High Similarity	NPC269886
0.9435	High Similarity	NPC81802
0.9435	High Similarity	NPC472295
0.866	High Similarity	NPC472291
0.8449	Intermediate Similarity	NPC220151
0.8449	Intermediate Similarity	NPC19692
0.8235	Intermediate Similarity	NPC314333
0.8235	Intermediate Similarity	NPC472112
0.8211	Intermediate Similarity	NPC102592
0.8211	Intermediate Similarity	NPC79356
0.8187	Intermediate Similarity	NPC471944
0.8098	Intermediate Similarity	NPC469896
0.8053	Intermediate Similarity	NPC472113
0.8045	Intermediate Similarity	NPC115232
0.8042	Intermediate Similarity	NPC329858
0.7989	Intermediate Similarity	NPC111602
0.7989	Intermediate Similarity	NPC102338
0.7989	Intermediate Similarity	NPC145885
0.7989	Intermediate Similarity	NPC63199
0.7989	Intermediate Similarity	NPC196251
0.7989	Intermediate Similarity	NPC84827
0.7989	Intermediate Similarity	NPC14113
0.797	Intermediate Similarity	NPC477979
0.7949	Intermediate Similarity	NPC128265
0.7949	Intermediate Similarity	NPC199851
0.7949	Intermediate Similarity	NPC294909
0.7949	Intermediate Similarity	NPC254240
0.7949	Intermediate Similarity	NPC312870
0.7927	Intermediate Similarity	NPC472116
0.7926	Intermediate Similarity	NPC133003
0.7884	Intermediate Similarity	NPC235684
0.7872	Intermediate Similarity	NPC477003
0.7865	Intermediate Similarity	NPC55493
0.7853	Intermediate Similarity	NPC324091
0.7849	Intermediate Similarity	NPC219336
0.7838	Intermediate Similarity	NPC151635
0.7835	Intermediate Similarity	NPC245916
0.7814	Intermediate Similarity	NPC471943
0.7812	Intermediate Similarity	NPC138370
0.7801	Intermediate Similarity	NPC175474
0.7796	Intermediate Similarity	NPC183662
0.7796	Intermediate Similarity	NPC15573
0.7796	Intermediate Similarity	NPC284775
0.7796	Intermediate Similarity	NPC217372
0.779	Intermediate Similarity	NPC271797
0.779	Intermediate Similarity	NPC21174
0.7789	Intermediate Similarity	NPC132539
0.7778	Intermediate Similarity	NPC258480
0.7755	Intermediate Similarity	NPC52557
0.7754	Intermediate Similarity	NPC126709
0.7754	Intermediate Similarity	NPC248041
0.7754	Intermediate Similarity	NPC283219
0.7742	Intermediate Similarity	NPC267885
0.7735	Intermediate Similarity	NPC214106
0.772	Intermediate Similarity	NPC476460
0.7696	Intermediate Similarity	NPC160381
0.7692	Intermediate Similarity	NPC202812
0.7688	Intermediate Similarity	NPC162730
0.7688	Intermediate Similarity	NPC203468
0.7688	Intermediate Similarity	NPC110500
0.7688	Intermediate Similarity	NPC149155
0.7673	Intermediate Similarity	NPC266249
0.7672	Intermediate Similarity	NPC191415
0.766	Intermediate Similarity	NPC213468
0.766	Intermediate Similarity	NPC55772
0.7656	Intermediate Similarity	NPC472323
0.7634	Intermediate Similarity	NPC252572
0.7626	Intermediate Similarity	NPC241024
0.7626	Intermediate Similarity	NPC81535
0.7626	Intermediate Similarity	NPC74413
0.7619	Intermediate Similarity	NPC91179
0.7617	Intermediate Similarity	NPC221873
0.7606	Intermediate Similarity	NPC234987
0.7604	Intermediate Similarity	NPC66210
0.76	Intermediate Similarity	NPC474116
0.7598	Intermediate Similarity	NPC123839
0.7592	Intermediate Similarity	NPC228835
0.7588	Intermediate Similarity	NPC49196
0.7588	Intermediate Similarity	NPC313985
0.7588	Intermediate Similarity	NPC214428
0.7588	Intermediate Similarity	NPC79129
0.7588	Intermediate Similarity	NPC249150
0.7588	Intermediate Similarity	NPC195461
0.7588	Intermediate Similarity	NPC81654
0.7585	Intermediate Similarity	NPC36405
0.7581	Intermediate Similarity	NPC6982
0.7574	Intermediate Similarity	NPC277350
0.7568	Intermediate Similarity	NPC78020
0.7565	Intermediate Similarity	NPC278434
0.7562	Intermediate Similarity	NPC165599
0.7551	Intermediate Similarity	NPC267343
0.7551	Intermediate Similarity	NPC304203
0.7549	Intermediate Similarity	NPC469743
0.754	Intermediate Similarity	NPC161861
0.7539	Intermediate Similarity	NPC159125
0.7539	Intermediate Similarity	NPC143533
0.7537	Intermediate Similarity	NPC477065
0.7526	Intermediate Similarity	NPC321708
0.7526	Intermediate Similarity	NPC15840
0.7525	Intermediate Similarity	NPC141454
0.7525	Intermediate Similarity	NPC167710
0.7524	Intermediate Similarity	NPC118940
0.7512	Intermediate Similarity	NPC260900
0.7512	Intermediate Similarity	NPC476874
0.7512	Intermediate Similarity	NPC137589
0.75	Intermediate Similarity	NPC46895
0.75	Intermediate Similarity	NPC472119
0.7488	Intermediate Similarity	NPC221100
0.7488	Intermediate Similarity	NPC234078
0.7487	Intermediate Similarity	NPC50503
0.7487	Intermediate Similarity	NPC154339
0.7475	Intermediate Similarity	NPC11445
0.7475	Intermediate Similarity	NPC317701
0.7473	Intermediate Similarity	NPC76982
0.7464	Intermediate Similarity	NPC312645
0.7461	Intermediate Similarity	NPC280290
0.7459	Intermediate Similarity	NPC42372
0.7451	Intermediate Similarity	NPC244741
0.7448	Intermediate Similarity	NPC117027
0.7448	Intermediate Similarity	NPC102755
0.7442	Intermediate Similarity	NPC194740
0.7437	Intermediate Similarity	NPC227582
0.7436	Intermediate Similarity	NPC473666
0.7424	Intermediate Similarity	NPC157828
0.7424	Intermediate Similarity	NPC195239
0.7421	Intermediate Similarity	NPC111275
0.7419	Intermediate Similarity	NPC49954
0.7419	Intermediate Similarity	NPC474561
0.7418	Intermediate Similarity	NPC285469
0.7409	Intermediate Similarity	NPC21429
0.7407	Intermediate Similarity	NPC293216
0.7404	Intermediate Similarity	NPC89508
0.74	Intermediate Similarity	NPC306376
0.7396	Intermediate Similarity	NPC113626
0.7395	Intermediate Similarity	NPC478078
0.7391	Intermediate Similarity	NPC82370
0.7389	Intermediate Similarity	NPC476115
0.7385	Intermediate Similarity	NPC70155
0.7382	Intermediate Similarity	NPC11126
0.7379	Intermediate Similarity	NPC271862
0.7379	Intermediate Similarity	NPC478158
0.7374	Intermediate Similarity	NPC326422
0.7371	Intermediate Similarity	NPC472107
0.7371	Intermediate Similarity	NPC282103
0.7371	Intermediate Similarity	NPC79062
0.7368	Intermediate Similarity	NPC474412
0.7366	Intermediate Similarity	NPC71132
0.7366	Intermediate Similarity	NPC474905
0.7363	Intermediate Similarity	NPC477004
0.7358	Intermediate Similarity	NPC470205
0.7356	Intermediate Similarity	NPC6865
0.7356	Intermediate Similarity	NPC471194
0.7356	Intermediate Similarity	NPC471193
0.7356	Intermediate Similarity	NPC153980
0.735	Intermediate Similarity	NPC262898
0.7346	Intermediate Similarity	NPC281049
0.7344	Intermediate Similarity	NPC88110
0.7344	Intermediate Similarity	NPC61011
0.7343	Intermediate Similarity	NPC234999
0.7337	Intermediate Similarity	NPC474121
0.7336	Intermediate Similarity	NPC229893
0.7336	Intermediate Similarity	NPC475271
0.7333	Intermediate Similarity	NPC135601
0.7333	Intermediate Similarity	NPC148183
0.7333	Intermediate Similarity	NPC94752
0.7333	Intermediate Similarity	NPC17273
0.7333	Intermediate Similarity	NPC152768
0.7333	Intermediate Similarity	NPC141612
0.7327	Intermediate Similarity	NPC252338
0.7326	Intermediate Similarity	NPC470509
0.7323	Intermediate Similarity	NPC67551
0.7323	Intermediate Similarity	NPC47190
0.7321	Intermediate Similarity	NPC229348
0.7317	Intermediate Similarity	NPC82053
0.7317	Intermediate Similarity	NPC471191
0.7313	Intermediate Similarity	NPC67288
0.7312	Intermediate Similarity	NPC8104
0.731	Intermediate Similarity	NPC83111
0.7308	Intermediate Similarity	NPC281094
0.7308	Intermediate Similarity	NPC72956
0.7302	Intermediate Similarity	NPC21638
0.73	Intermediate Similarity	NPC179701
0.7299	Intermediate Similarity	NPC472285
0.7296	Intermediate Similarity	NPC17059
0.7288	Intermediate Similarity	NPC58268
0.7288	Intermediate Similarity	NPC114033
0.7288	Intermediate Similarity	NPC101130
0.7288	Intermediate Similarity	NPC129412
0.7277	Intermediate Similarity	NPC237414
0.7277	Intermediate Similarity	NPC323969
0.7277	Intermediate Similarity	NPC293917
0.7273	Intermediate Similarity	NPC475778
0.7273	Intermediate Similarity	NPC473493
0.7268	Intermediate Similarity	NPC473376
0.7264	Intermediate Similarity	NPC82070

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 NPC472293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	540
0.2-0.3	869
0.3-0.4	1840
0.4-0.5	2746
0.5-0.6	2161
0.6-0.7	726
0.7-0.8	82
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
0.8235	Intermediate Similarity	NPD4499	Approved
0.801	Intermediate Similarity	NPD6176	Phase 1
0.7949	Intermediate Similarity	NPD4500	Approved
0.7949	Intermediate Similarity	NPD4501	Approved
0.7931	Intermediate Similarity	NPD3389	Approved
0.7931	Intermediate Similarity	NPD3393	Approved
0.7931	Intermediate Similarity	NPD3394	Approved
0.785	Intermediate Similarity	NPD2509	Approved
0.785	Intermediate Similarity	NPD2510	Approved
0.7821	Intermediate Similarity	NPD1630	Approved
0.7819	Intermediate Similarity	NPD2094	Phase 2
0.7819	Intermediate Similarity	NPD2095	Phase 2
0.7819	Intermediate Similarity	NPD2092	Phase 2
0.7819	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2091	Phase 2
0.7778	Intermediate Similarity	NPD2096	Phase 2
0.7739	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5901	Discontinued
0.7692	Intermediate Similarity	NPD1631	Approved
0.7688	Intermediate Similarity	NPD482	Approved
0.7647	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4506	Discontinued
0.7622	Intermediate Similarity	NPD1575	Approved
0.7622	Intermediate Similarity	NPD1573	Approved
0.7619	Intermediate Similarity	NPD5473	Discontinued
0.7598	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4600	Approved
0.7588	Intermediate Similarity	NPD4601	Approved
0.756	Intermediate Similarity	NPD6770	Approved
0.754	Intermediate Similarity	NPD750	Phase 2
0.75	Intermediate Similarity	NPD1586	Approved
0.75	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4948	Discontinued
0.744	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3947	Discontinued
0.74	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD4848	Phase 1
0.7382	Intermediate Similarity	NPD1587	Approved
0.7366	Intermediate Similarity	NPD2915	Discontinued
0.7358	Intermediate Similarity	NPD3319	Phase 1
0.7358	Intermediate Similarity	NPD3318	Approved
0.7358	Intermediate Similarity	NPD3320	Approved
0.7337	Intermediate Similarity	NPD2213	Approved
0.7337	Intermediate Similarity	NPD2214	Approved
0.7333	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7470	Discontinued
0.7287	Intermediate Similarity	NPD2844	Phase 3
0.7277	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2336	Approved
0.7273	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8115	Approved
0.7268	Intermediate Similarity	NPD8114	Approved
0.7263	Intermediate Similarity	NPD4524	Discontinued
0.7233	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD8072	Approved
0.7216	Intermediate Similarity	NPD3178	Discontinued
0.7206	Intermediate Similarity	NPD7817	Phase 1
0.7206	Intermediate Similarity	NPD7727	Phase 2
0.7204	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6242	Discontinued
0.719	Intermediate Similarity	NPD7455	Approved
0.719	Intermediate Similarity	NPD7454	Approved
0.7184	Intermediate Similarity	NPD6987	Phase 1
0.7171	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8073	Approved
0.7164	Intermediate Similarity	NPD4602	Approved
0.7158	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6479	Discontinued
0.7143	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5475	Discontinued
0.7129	Intermediate Similarity	NPD2307	Discontinued
0.7123	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5104	Approved
0.7098	Intermediate Similarity	NPD4075	Phase 2
0.7095	Intermediate Similarity	NPD5072	Discontinued
0.7081	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7994	Phase 2
0.7077	Intermediate Similarity	NPD5897	Approved
0.7077	Intermediate Similarity	NPD5899	Approved
0.7077	Intermediate Similarity	NPD5898	Approved
0.7077	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2008	Discontinued
0.7067	Intermediate Similarity	NPD7957	Phase 1
0.7062	Intermediate Similarity	NPD2144	Approved
0.7044	Intermediate Similarity	NPD6226	Phase 3
0.7041	Intermediate Similarity	NPD3038	Discontinued
0.7035	Intermediate Similarity	NPD4988	Discontinued
0.7028	Intermediate Similarity	NPD8097	Phase 3
0.7028	Intermediate Similarity	NPD2411	Approved
0.7028	Intermediate Similarity	NPD8096	Phase 3
0.7026	Intermediate Similarity	NPD4076	Approved
0.7026	Intermediate Similarity	NPD4079	Approved
0.7024	Intermediate Similarity	NPD6249	Phase 2
0.7024	Intermediate Similarity	NPD6248	Phase 2
0.7023	Intermediate Similarity	NPD7878	Phase 2
0.7019	Intermediate Similarity	NPD8098	Approved
0.7019	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4952	Phase 3
0.701	Intermediate Similarity	NPD5003	Discontinued
0.7	Intermediate Similarity	NPD1534	Approved
0.7	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4334	Discontinued
0.7	Intermediate Similarity	NPD6486	Approved
0.7	Intermediate Similarity	NPD6487	Approved
0.6991	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.699	Remote Similarity	NPD484	Approved
0.6985	Remote Similarity	NPD5809	Phase 3
0.6981	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3506	Approved
0.6974	Remote Similarity	NPD3505	Approved
0.6972	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7941	Phase 3
0.6961	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1996	Discontinued
0.6957	Remote Similarity	NPD3100	Discontinued
0.6951	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5632	Approved
0.6943	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5426	Phase 3
0.6935	Remote Similarity	NPD5075	Discontinued
0.6927	Remote Similarity	NPD6664	Approved
0.6923	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4373	Phase 2
0.6919	Remote Similarity	NPD4462	Approved
0.6919	Remote Similarity	NPD6376	Discontinued
0.6919	Remote Similarity	NPD4463	Approved
0.6919	Remote Similarity	NPD7232	Discontinued
0.6916	Remote Similarity	NPD3795	Approved
0.6916	Remote Similarity	NPD3794	Approved
0.6912	Remote Similarity	NPD7619	Phase 3
0.6912	Remote Similarity	NPD7618	Phase 3
0.6906	Remote Similarity	NPD7688	Phase 1
0.6904	Remote Similarity	NPD6595	Phase 3
0.69	Remote Similarity	NPD5444	Phase 1
0.6898	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD786	Approved
0.6884	Remote Similarity	NPD3436	Approved
0.6884	Remote Similarity	NPD5293	Phase 2
0.6884	Remote Similarity	NPD7564	Discontinued
0.6884	Remote Similarity	NPD721	Approved
0.6872	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5866	Approved
0.6869	Remote Similarity	NPD3435	Discontinued
0.6866	Remote Similarity	NPD3961	Discontinued
0.6864	Remote Similarity	NPD6173	Approved
0.6863	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD3006	Discontinued
0.6858	Remote Similarity	NPD7853	Phase 2
0.6857	Remote Similarity	NPD8272	Phase 2
0.6854	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8160	Phase 2
0.6847	Remote Similarity	NPD3259	Approved
0.6847	Remote Similarity	NPD4845	Discontinued
0.6842	Remote Similarity	NPD3773	Approved
0.6842	Remote Similarity	NPD3774	Approved
0.6842	Remote Similarity	NPD3775	Approved
0.6834	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7234	Approved
0.6832	Remote Similarity	NPD7233	Approved
0.6832	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5254	Discontinued
0.6829	Remote Similarity	NPD7944	Discontinued
0.6825	Remote Similarity	NPD7568	Phase 1
0.6825	Remote Similarity	NPD4326	Phase 2
0.6824	Remote Similarity	NPD5482	Discontinued
0.6823	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.682	Remote Similarity	NPD5818	Discontinued
0.6818	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2479	Phase 3
0.6818	Remote Similarity	NPD2481	Approved
0.6814	Remote Similarity	NPD4922	Phase 2
0.6814	Remote Similarity	NPD6665	Discontinued
0.6814	Remote Similarity	NPD5505	Discontinued
0.6814	Remote Similarity	NPD4315	Phase 2
0.6813	Remote Similarity	NPD5020	Approved
0.6813	Remote Similarity	NPD1722	Approved
0.6812	Remote Similarity	NPD4397	Phase 1
0.6812	Remote Similarity	NPD53	Approved
0.6812	Remote Similarity	NPD7777	Approved
0.6812	Remote Similarity	NPD7778	Approved
0.6809	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7970	Approved
0.6804	Remote Similarity	NPD1325	Approved
0.6804	Remote Similarity	NPD1326	Approved

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