NPASS Compound

Structure

NPC472297 OpenBabel07101718202D 26 29 0 0 1 0 0 0 0 0999 V2000 -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 -2.5546 0.1713 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 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 2 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 22 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 2 0 0 0 0 6 15 2 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 8 1 1 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 21 1 0 0 0 0 16 7 1 6 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 1 0 0 0 19 21 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.14
Volume:	356.313
LogP:	2.311
LogD:	1.743
LogS:	-3.301
# 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:	0.661
Synthetic Accessibility Score:	4.722
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.844
MDCK Permeability:	3.104890856775455e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.092
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.167
30% Bioavailability (F30%):	0.373

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	57.09197235107422%
Volume Distribution (VD):	1.598
Pgp-substrate:	60.678226470947266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.818
CYP1A2-substrate:	0.522
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.781
CYP3A4-inhibitor:	0.442
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	6.698
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.505
Drug-inuced Liver Injury (DILI):	0.405
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.792
Carcinogencity:	0.894
Eye Corrosion:	0.136
Eye Irritation:	0.265
Respiratory Toxicity:	0.991

Download Data

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

Natural Product: NPC472297

Natural Product ID:	NPC472297
*Common Name:**	YQIXIDJOTMBOLU-RPVQJOFSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YQIXIDJOTMBOLU-RPVQJOFSSA-N
Standard InCHI:	InChI=1S/C20H20N2O4/c1-22-9-11(10-23)13-8-17(24)19-14(7-16(22)18(13)20(25)26-2)12-5-3-4-6-15(12)21-19/h3-6,9-10,13,16,18,21H,7-8H2,1-2H3/t13-,16+,18-/m1/s1
SMILES:	COC(=O)[C@H]1[C@@H]2Cc3c(C(=O)C[C@@H]1C(=CN2C)C=O)[nH]c1c3cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358051
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	=	5.1	ug.mL-1	PMID[573948]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[573948]

☑ 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 NPC472297 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	293
0.1-0.2	2169
0.2-0.3	12102
0.3-0.4	18678
0.4-0.5	4982
0.5-0.6	2337
0.6-0.7	1732
0.7-0.8	386
0.8-0.85	7
0.85-0.9	2
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472296
0.983	High Similarity	NPC472293
0.9659	High Similarity	NPC472292
0.9278	High Similarity	NPC247735
0.9278	High Similarity	NPC81802
0.9278	High Similarity	NPC269886
0.9278	High Similarity	NPC472295
0.9278	High Similarity	NPC472210
0.8622	High Similarity	NPC472291
0.861	High Similarity	NPC19692
0.861	High Similarity	NPC220151
0.8211	Intermediate Similarity	NPC472113
0.8201	Intermediate Similarity	NPC472112
0.8105	Intermediate Similarity	NPC314333
0.8083	Intermediate Similarity	NPC102592
0.8083	Intermediate Similarity	NPC79356
0.8061	Intermediate Similarity	NPC471944
0.7968	Intermediate Similarity	NPC469896
0.7958	Intermediate Similarity	NPC63199
0.7958	Intermediate Similarity	NPC111602
0.7958	Intermediate Similarity	NPC102338
0.7958	Intermediate Similarity	NPC196251
0.7941	Intermediate Similarity	NPC477979
0.7919	Intermediate Similarity	NPC294909
0.7919	Intermediate Similarity	NPC128265
0.7919	Intermediate Similarity	NPC312870
0.7919	Intermediate Similarity	NPC254240
0.7919	Intermediate Similarity	NPC199851
0.7917	Intermediate Similarity	NPC329858
0.7912	Intermediate Similarity	NPC115232
0.7861	Intermediate Similarity	NPC14113
0.7861	Intermediate Similarity	NPC145885
0.7861	Intermediate Similarity	NPC84827
0.7835	Intermediate Similarity	NPC55493
0.7806	Intermediate Similarity	NPC472116
0.7806	Intermediate Similarity	NPC245916
0.7801	Intermediate Similarity	NPC133003
0.7772	Intermediate Similarity	NPC175474
0.7766	Intermediate Similarity	NPC234987
0.776	Intermediate Similarity	NPC235684
0.776	Intermediate Similarity	NPC66210
0.7749	Intermediate Similarity	NPC477003
0.7749	Intermediate Similarity	NPC258480
0.7732	Intermediate Similarity	NPC324091
0.7727	Intermediate Similarity	NPC52557
0.7725	Intermediate Similarity	NPC219336
0.7713	Intermediate Similarity	NPC151635
0.7696	Intermediate Similarity	NPC159125
0.7692	Intermediate Similarity	NPC138370
0.7688	Intermediate Similarity	NPC471943
0.7673	Intermediate Similarity	NPC132539
0.7672	Intermediate Similarity	NPC217372
0.7672	Intermediate Similarity	NPC15573
0.7672	Intermediate Similarity	NPC284775
0.7672	Intermediate Similarity	NPC183662
0.7663	Intermediate Similarity	NPC21174
0.7663	Intermediate Similarity	NPC271797
0.7662	Intermediate Similarity	NPC162730
0.7637	Intermediate Similarity	NPC76982
0.7632	Intermediate Similarity	NPC248041
0.7632	Intermediate Similarity	NPC283219
0.7632	Intermediate Similarity	NPC126709
0.7629	Intermediate Similarity	NPC472323
0.7622	Intermediate Similarity	NPC42372
0.7619	Intermediate Similarity	NPC267885
0.7609	Intermediate Similarity	NPC214106
0.7604	Intermediate Similarity	NPC102755
0.7602	Intermediate Similarity	NPC476460
0.76	Intermediate Similarity	NPC241024
0.7577	Intermediate Similarity	NPC160381
0.7576	Intermediate Similarity	NPC202812
0.7574	Intermediate Similarity	NPC474116
0.7573	Intermediate Similarity	NPC123839
0.7566	Intermediate Similarity	NPC149155
0.7566	Intermediate Similarity	NPC203468
0.7566	Intermediate Similarity	NPC293216
0.7566	Intermediate Similarity	NPC110500
0.7562	Intermediate Similarity	NPC313985
0.7562	Intermediate Similarity	NPC49196
0.7562	Intermediate Similarity	NPC214428
0.7562	Intermediate Similarity	NPC81654
0.7562	Intermediate Similarity	NPC249150
0.7562	Intermediate Similarity	NPC195461
0.7562	Intermediate Similarity	NPC79129
0.7561	Intermediate Similarity	NPC266249
0.7552	Intermediate Similarity	NPC113626
0.7552	Intermediate Similarity	NPC191415
0.7549	Intermediate Similarity	NPC277350
0.7539	Intermediate Similarity	NPC55772
0.7539	Intermediate Similarity	NPC213468
0.7537	Intermediate Similarity	NPC165599
0.7526	Intermediate Similarity	NPC472107
0.7526	Intermediate Similarity	NPC79062
0.7525	Intermediate Similarity	NPC267343
0.7524	Intermediate Similarity	NPC469743
0.7513	Intermediate Similarity	NPC252572
0.7512	Intermediate Similarity	NPC81535
0.7512	Intermediate Similarity	NPC74413
0.75	Intermediate Similarity	NPC221873
0.75	Intermediate Similarity	NPC15840
0.75	Intermediate Similarity	NPC88110
0.75	Intermediate Similarity	NPC118940
0.75	Intermediate Similarity	NPC91179
0.7488	Intermediate Similarity	NPC476874
0.7476	Intermediate Similarity	NPC36405
0.7474	Intermediate Similarity	NPC472119
0.7474	Intermediate Similarity	NPC228835
0.7464	Intermediate Similarity	NPC234078
0.7464	Intermediate Similarity	NPC221100
0.7463	Intermediate Similarity	NPC50503
0.7462	Intermediate Similarity	NPC154339
0.746	Intermediate Similarity	NPC6982
0.7458	Intermediate Similarity	NPC101130
0.7458	Intermediate Similarity	NPC114033
0.7458	Intermediate Similarity	NPC58268
0.7458	Intermediate Similarity	NPC129412
0.7449	Intermediate Similarity	NPC278434
0.7447	Intermediate Similarity	NPC78020
0.7441	Intermediate Similarity	NPC472285
0.7441	Intermediate Similarity	NPC312645
0.7437	Intermediate Similarity	NPC304203
0.7427	Intermediate Similarity	NPC244741
0.7427	Intermediate Similarity	NPC477065
0.7423	Intermediate Similarity	NPC143533
0.7421	Intermediate Similarity	NPC161861
0.7413	Intermediate Similarity	NPC167710
0.7413	Intermediate Similarity	NPC141454
0.7411	Intermediate Similarity	NPC321708
0.7402	Intermediate Similarity	NPC260900
0.7402	Intermediate Similarity	NPC137589
0.7385	Intermediate Similarity	NPC46895
0.7381	Intermediate Similarity	NPC89508
0.7371	Intermediate Similarity	NPC470677
0.7366	Intermediate Similarity	NPC317701
0.7366	Intermediate Similarity	NPC476115
0.7364	Intermediate Similarity	NPC70155
0.7363	Intermediate Similarity	NPC11445
0.7356	Intermediate Similarity	NPC271862
0.7356	Intermediate Similarity	NPC478158
0.7347	Intermediate Similarity	NPC280290
0.7343	Intermediate Similarity	NPC474905
0.7339	Intermediate Similarity	NPC194740
0.7333	Intermediate Similarity	NPC117027
0.7327	Intermediate Similarity	NPC227582
0.7326	Intermediate Similarity	NPC242116
0.7324	Intermediate Similarity	NPC281049
0.7323	Intermediate Similarity	NPC473666
0.7321	Intermediate Similarity	NPC234999
0.7315	Intermediate Similarity	NPC475271
0.7313	Intermediate Similarity	NPC195239
0.7313	Intermediate Similarity	NPC474121
0.7313	Intermediate Similarity	NPC157828
0.7311	Intermediate Similarity	NPC148183
0.7311	Intermediate Similarity	NPC152768
0.7306	Intermediate Similarity	NPC111275
0.7302	Intermediate Similarity	NPC474561
0.7302	Intermediate Similarity	NPC49954
0.7302	Intermediate Similarity	NPC114637
0.73	Intermediate Similarity	NPC67551
0.7299	Intermediate Similarity	NPC229348
0.7297	Intermediate Similarity	NPC285469
0.7296	Intermediate Similarity	NPC21429
0.7294	Intermediate Similarity	NPC478078
0.7291	Intermediate Similarity	NPC306376
0.7286	Intermediate Similarity	NPC82370
0.7281	Intermediate Similarity	NPC21638
0.7268	Intermediate Similarity	NPC11126
0.7264	Intermediate Similarity	NPC474412
0.7264	Intermediate Similarity	NPC326422
0.7259	Intermediate Similarity	NPC282103
0.7255	Intermediate Similarity	NPC477004
0.7255	Intermediate Similarity	NPC477045
0.7251	Intermediate Similarity	NPC153980
0.7251	Intermediate Similarity	NPC471193
0.7251	Intermediate Similarity	NPC475778
0.7251	Intermediate Similarity	NPC471194
0.7251	Intermediate Similarity	NPC6865
0.7249	Intermediate Similarity	NPC71132
0.7245	Intermediate Similarity	NPC470205
0.7243	Intermediate Similarity	NPC82070
0.7241	Intermediate Similarity	NPC262898
0.7235	Intermediate Similarity	NPC229893
0.7231	Intermediate Similarity	NPC61011
0.723	Intermediate Similarity	NPC476114
0.723	Intermediate Similarity	NPC471192
0.7225	Intermediate Similarity	NPC258062
0.7225	Intermediate Similarity	NPC127677
0.7222	Intermediate Similarity	NPC94752
0.7222	Intermediate Similarity	NPC17273
0.7222	Intermediate Similarity	NPC315555
0.7222	Intermediate Similarity	NPC141612
0.7222	Intermediate Similarity	NPC135601
0.722	Intermediate Similarity	NPC252338
0.7217	Intermediate Similarity	NPC54744
0.7214	Intermediate Similarity	NPC47190
0.7212	Intermediate Similarity	NPC471191
0.7212	Intermediate Similarity	NPC82053
0.7211	Intermediate Similarity	NPC470509
0.7209	Intermediate Similarity	NPC52254
0.7206	Intermediate Similarity	NPC67288

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 NPC472297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	550
0.2-0.3	874
0.3-0.4	1894
0.4-0.5	2783
0.5-0.6	2137
0.6-0.7	666
0.7-0.8	67
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
0.8105	Intermediate Similarity	NPD4499	Approved
0.798	Intermediate Similarity	NPD6176	Phase 1
0.7919	Intermediate Similarity	NPD4500	Approved
0.7919	Intermediate Similarity	NPD4501	Approved
0.7902	Intermediate Similarity	NPD3394	Approved
0.7902	Intermediate Similarity	NPD3389	Approved
0.7902	Intermediate Similarity	NPD3393	Approved
0.7822	Intermediate Similarity	NPD2509	Approved
0.7822	Intermediate Similarity	NPD2510	Approved
0.7711	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD2092	Phase 2
0.7696	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD2094	Phase 2
0.7696	Intermediate Similarity	NPD2095	Phase 2
0.7692	Intermediate Similarity	NPD1630	Approved
0.7656	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD2096	Phase 2
0.7656	Intermediate Similarity	NPD2091	Phase 2
0.761	Intermediate Similarity	NPD4506	Discontinued
0.7586	Intermediate Similarity	NPD5901	Discontinued
0.7568	Intermediate Similarity	NPD1631	Approved
0.7566	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD482	Approved
0.7562	Intermediate Similarity	NPD4600	Approved
0.7562	Intermediate Similarity	NPD4601	Approved
0.7536	Intermediate Similarity	NPD6770	Approved
0.7526	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1573	Approved
0.75	Intermediate Similarity	NPD1575	Approved
0.75	Intermediate Similarity	NPD5473	Discontinued
0.7488	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD750	Phase 2
0.7416	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3947	Discontinued
0.7389	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD1586	Approved
0.736	Intermediate Similarity	NPD4948	Discontinued
0.7312	Intermediate Similarity	NPD2214	Approved
0.7312	Intermediate Similarity	NPD2213	Approved
0.7291	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7470	Discontinued
0.7277	Intermediate Similarity	NPD4848	Phase 1
0.7268	Intermediate Similarity	NPD1587	Approved
0.7255	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD2915	Discontinued
0.7246	Intermediate Similarity	NPD8114	Approved
0.7246	Intermediate Similarity	NPD8115	Approved
0.7245	Intermediate Similarity	NPD3319	Phase 1
0.7245	Intermediate Similarity	NPD3320	Approved
0.7245	Intermediate Similarity	NPD3318	Approved
0.7222	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8072	Approved
0.7184	Intermediate Similarity	NPD7727	Phase 2
0.7184	Intermediate Similarity	NPD7817	Phase 1
0.7183	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD2844	Phase 3
0.7171	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7455	Approved
0.717	Intermediate Similarity	NPD7454	Approved
0.7164	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2336	Approved
0.7164	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4524	Discontinued
0.715	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6479	Discontinued
0.7123	Intermediate Similarity	NPD5475	Discontinued
0.7107	Intermediate Similarity	NPD3178	Discontinued
0.7097	Intermediate Similarity	NPD6242	Discontinued
0.7081	Intermediate Similarity	NPD6987	Phase 1
0.7077	Intermediate Similarity	NPD5104	Approved
0.7075	Intermediate Similarity	NPD5072	Discontinued
0.7067	Intermediate Similarity	NPD8073	Approved
0.7062	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4602	Approved
0.7059	Intermediate Similarity	NPD7994	Phase 2
0.7056	Intermediate Similarity	NPD5899	Approved
0.7056	Intermediate Similarity	NPD5898	Approved
0.7056	Intermediate Similarity	NPD5897	Approved
0.7048	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7957	Phase 1
0.7047	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2144	Approved
0.7031	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2307	Discontinued
0.7023	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3038	Discontinued
0.7019	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4079	Approved
0.7005	Intermediate Similarity	NPD7878	Phase 2
0.7005	Intermediate Similarity	NPD6249	Phase 2
0.7005	Intermediate Similarity	NPD6248	Phase 2
0.7005	Intermediate Similarity	NPD4076	Approved
0.6996	Remote Similarity	NPD4952	Phase 3
0.6995	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4075	Phase 2
0.699	Remote Similarity	NPD5003	Discontinued
0.698	Remote Similarity	NPD4334	Discontinued
0.6974	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2008	Discontinued
0.6967	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3506	Approved
0.6954	Remote Similarity	NPD3505	Approved
0.6942	Remote Similarity	NPD6226	Phase 3
0.6941	Remote Similarity	NPD1996	Discontinued
0.6931	Remote Similarity	NPD4988	Discontinued
0.693	Remote Similarity	NPD2411	Approved
0.693	Remote Similarity	NPD8097	Phase 3
0.693	Remote Similarity	NPD8096	Phase 3
0.6927	Remote Similarity	NPD5632	Approved
0.6926	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8098	Approved
0.6919	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5075	Discontinued
0.6906	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4373	Phase 2
0.6901	Remote Similarity	NPD6486	Approved
0.6901	Remote Similarity	NPD6487	Approved
0.6898	Remote Similarity	NPD3795	Approved
0.6898	Remote Similarity	NPD3794	Approved
0.6897	Remote Similarity	NPD1534	Approved
0.6893	Remote Similarity	NPD7944	Discontinued
0.6891	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.689	Remote Similarity	NPD484	Approved
0.6889	Remote Similarity	NPD7688	Phase 1
0.6881	Remote Similarity	NPD5809	Phase 3
0.6881	Remote Similarity	NPD5444	Phase 1
0.6869	Remote Similarity	NPD7941	Phase 3
0.6866	Remote Similarity	NPD5293	Phase 2
0.6866	Remote Similarity	NPD3436	Approved
0.686	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3435	Discontinued
0.6847	Remote Similarity	NPD3246	Discontinued
0.6845	Remote Similarity	NPD3100	Discontinued
0.6842	Remote Similarity	NPD3006	Discontinued
0.6842	Remote Similarity	NPD7853	Phase 2
0.684	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.684	Remote Similarity	NPD5426	Phase 3
0.684	Remote Similarity	NPD8272	Phase 2
0.6837	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8160	Phase 2
0.6831	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6664	Approved
0.6822	Remote Similarity	NPD6376	Discontinued
0.6822	Remote Similarity	NPD7232	Discontinued
0.6814	Remote Similarity	NPD7234	Approved
0.6814	Remote Similarity	NPD7233	Approved
0.6812	Remote Similarity	NPD7619	Phase 3
0.6812	Remote Similarity	NPD7618	Phase 3
0.6809	Remote Similarity	NPD5482	Discontinued
0.6809	Remote Similarity	NPD4463	Approved
0.6809	Remote Similarity	NPD4462	Approved
0.6804	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6595	Phase 3
0.6796	Remote Similarity	NPD4315	Phase 2
0.6794	Remote Similarity	NPD53	Approved
0.6794	Remote Similarity	NPD7778	Approved
0.6794	Remote Similarity	NPD7777	Approved
0.6782	Remote Similarity	NPD7564	Discontinued
0.6782	Remote Similarity	NPD721	Approved
0.678	Remote Similarity	NPD2565	Phase 2
0.678	Remote Similarity	NPD2564	Approved
0.6779	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8322	Phase 2
0.6776	Remote Similarity	NPD786	Approved
0.6776	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5866	Approved
0.6773	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6173	Approved
0.6766	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3961	Discontinued
0.6763	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD4845	Discontinued
0.6756	Remote Similarity	NPD3259	Approved
0.6748	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD3774	Approved
0.6745	Remote Similarity	NPD3775	Approved
0.6745	Remote Similarity	NPD3773	Approved
0.6737	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7568	Phase 1
0.6729	Remote Similarity	NPD7001	Phase 3
0.6729	Remote Similarity	NPD7010	Phase 3
0.6729	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5818	Discontinued
0.6726	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5254	Discontinued
0.6719	Remote Similarity	NPD4326	Phase 2
0.6718	Remote Similarity	NPD5744	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