NPASS Compound

Structure

NPC476111 OpenBabel07101719252D 37 40 0 0 1 0 0 0 0 0999 V2000 0.0449 2.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7986 4.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2521 -1.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 0.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9033 2.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -1.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5305 4.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4188 3.0515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4921 -0.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4412 -3.1110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0938 -4.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8136 3.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3011 -1.3254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4452 -3.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -2.2764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8884 -1.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6870 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9921 -2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7019 2.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5454 3.5385 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1073 -4.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5799 -3.0854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 1.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3265 -1.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 27 1 0 0 0 0 7 27 1 0 0 0 0 8 30 1 0 0 0 0 9 30 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 18 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 31 1 0 0 0 0 14 22 2 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 16 28 1 6 0 0 0 17 32 2 0 0 0 0 17 37 1 0 0 0 0 19 11 1 1 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 28 1 1 0 0 0 21 24 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 30 1 0 0 0 0 23 33 2 0 0 0 0 24 27 1 0 0 0 0 24 29 1 1 0 0 0 25 29 1 1 0 0 0 25 36 1 0 0 0 0 26 34 2 0 0 0 0 26 36 1 0 0 0 0 27 29 1 0 0 0 0 28 35 1 6 0 0 0 29 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	515.29
Volume:	532.624
LogP:	3.131
LogD:	2.292
LogS:	-4.343
# Rotatable Bonds:	7
TPSA:	113.37
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	5.446
Fsp3:	0.69
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.927
MDCK Permeability:	2.6634035748429596e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.125
Human Intestinal Absorption (HIA):	0.837
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.436
Plasma Protein Binding (PPB):	38.58164978027344%
Volume Distribution (VD):	1.44
Pgp-substrate:	57.90174102783203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.206
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.504
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.361

ADMET: Excretion

Clearance (CL):	4.744
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.771
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.771
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.466
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC476111

Natural Product ID:	NPC476111
*Common Name:**	HHIRMXJEGFWTGN-VHQOBAGBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HHIRMXJEGFWTGN-VHQOBAGBSA-N
Standard InCHI:	InChI=1S/C29H41NO7/c1-14(2)22(30(8)9)26(34)36-25-16(4)28(35)20-10-15(3)23(33)19(20)11-18(13-31)12-21(28)24-27(6,7)29(24,25)37-17(5)32/h10,12,16,19-21,24-25,31,35H,11,13H2,1-9H3/t16-,19-,20-,21+,24-,25-,28+,29-/m1/s1
SMILES:	OCC1=C[C@H]2[C@@H]3C([C@]3(OC(=O)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@H](C1)C(=O)C(=C2)C)O)C)OC(=O)C(=C(C)C)N(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526931
PubChem CID:	44583798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO9267	Croton ciliatoglandulifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792405]
NPO9267	Croton ciliatoglandulifer	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	100000.0	nM	PMID[515676]

☑ 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 NPC476111 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	157
0.1-0.2	916
0.2-0.3	3605
0.3-0.4	9874
0.4-0.5	16178
0.5-0.6	8935
0.6-0.7	2760
0.7-0.8	190
0.8-0.85	57
0.85-0.9	21
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9435	High Similarity	NPC189393
0.9435	High Similarity	NPC90814
0.9141	High Similarity	NPC243902
0.876	High Similarity	NPC234858
0.876	High Similarity	NPC471127
0.876	High Similarity	NPC154363
0.8689	High Similarity	NPC10721
0.8595	High Similarity	NPC472757
0.8548	High Similarity	NPC236918
0.8548	High Similarity	NPC156745
0.8525	High Similarity	NPC472400
0.848	Intermediate Similarity	NPC471128
0.848	Intermediate Similarity	NPC329080
0.848	Intermediate Similarity	NPC475885
0.848	Intermediate Similarity	NPC471126
0.848	Intermediate Similarity	NPC145182
0.848	Intermediate Similarity	NPC157252
0.848	Intermediate Similarity	NPC472759
0.8468	Intermediate Similarity	NPC124676
0.8468	Intermediate Similarity	NPC146280
0.8413	Intermediate Similarity	NPC52839
0.832	Intermediate Similarity	NPC472397
0.832	Intermediate Similarity	NPC471125
0.832	Intermediate Similarity	NPC472758
0.832	Intermediate Similarity	NPC171905
0.8281	Intermediate Similarity	NPC472399
0.8254	Intermediate Similarity	NPC5991
0.8254	Intermediate Similarity	NPC5989
0.8254	Intermediate Similarity	NPC255081
0.8254	Intermediate Similarity	NPC22628
0.8254	Intermediate Similarity	NPC275696
0.8254	Intermediate Similarity	NPC471108
0.824	Intermediate Similarity	NPC156252
0.8217	Intermediate Similarity	NPC145238
0.8203	Intermediate Similarity	NPC162009
0.8203	Intermediate Similarity	NPC257017
0.8145	Intermediate Similarity	NPC71889
0.8125	Intermediate Similarity	NPC472401
0.808	Intermediate Similarity	NPC474872
0.8062	Intermediate Similarity	NPC19464
0.7984	Intermediate Similarity	NPC260786
0.7984	Intermediate Similarity	NPC96739
0.7984	Intermediate Similarity	NPC474871
0.7984	Intermediate Similarity	NPC174471
0.7984	Intermediate Similarity	NPC158523
0.7984	Intermediate Similarity	NPC475937
0.792	Intermediate Similarity	NPC101825
0.792	Intermediate Similarity	NPC215643
0.792	Intermediate Similarity	NPC151216
0.792	Intermediate Similarity	NPC170212
0.792	Intermediate Similarity	NPC221511
0.792	Intermediate Similarity	NPC89227
0.792	Intermediate Similarity	NPC475391
0.792	Intermediate Similarity	NPC17138
0.792	Intermediate Similarity	NPC265499
0.7907	Intermediate Similarity	NPC185876
0.7907	Intermediate Similarity	NPC19336
0.7903	Intermediate Similarity	NPC153036
0.7895	Intermediate Similarity	NPC270109
0.7891	Intermediate Similarity	NPC472760
0.7857	Intermediate Similarity	NPC474937
0.7829	Intermediate Similarity	NPC180640
0.7744	Intermediate Similarity	NPC222307
0.7692	Intermediate Similarity	NPC472667
0.7687	Intermediate Similarity	NPC204556
0.768	Intermediate Similarity	NPC273433
0.768	Intermediate Similarity	NPC163004
0.7674	Intermediate Similarity	NPC153651
0.7669	Intermediate Similarity	NPC473709
0.7669	Intermediate Similarity	NPC473919
0.7594	Intermediate Similarity	NPC473802
0.7578	Intermediate Similarity	NPC477091
0.7556	Intermediate Similarity	NPC471940
0.752	Intermediate Similarity	NPC67321
0.752	Intermediate Similarity	NPC187435
0.75	Intermediate Similarity	NPC143755
0.75	Intermediate Similarity	NPC236999
0.7481	Intermediate Similarity	NPC293112
0.7481	Intermediate Similarity	NPC9714
0.7481	Intermediate Similarity	NPC471939
0.7447	Intermediate Similarity	NPC246209
0.7444	Intermediate Similarity	NPC310511
0.7422	Intermediate Similarity	NPC469656
0.7422	Intermediate Similarity	NPC469655
0.7422	Intermediate Similarity	NPC474846
0.7405	Intermediate Similarity	NPC469684
0.7402	Intermediate Similarity	NPC218602
0.7381	Intermediate Similarity	NPC143609
0.7372	Intermediate Similarity	NPC470850
0.7364	Intermediate Similarity	NPC472002
0.7344	Intermediate Similarity	NPC257240
0.7344	Intermediate Similarity	NPC253906
0.7339	Intermediate Similarity	NPC476081
0.7333	Intermediate Similarity	NPC11895
0.7333	Intermediate Similarity	NPC469789
0.7328	Intermediate Similarity	NPC471816
0.7328	Intermediate Similarity	NPC470793
0.7328	Intermediate Similarity	NPC179626
0.7323	Intermediate Similarity	NPC306265
0.7319	Intermediate Similarity	NPC104382
0.7319	Intermediate Similarity	NPC470851
0.7313	Intermediate Similarity	NPC67569
0.7302	Intermediate Similarity	NPC111952
0.7293	Intermediate Similarity	NPC475041
0.7293	Intermediate Similarity	NPC469380
0.7279	Intermediate Similarity	NPC81736
0.7279	Intermediate Similarity	NPC172154
0.7273	Intermediate Similarity	NPC475323
0.7273	Intermediate Similarity	NPC473656
0.7273	Intermediate Similarity	NPC476558
0.7259	Intermediate Similarity	NPC170538
0.7259	Intermediate Similarity	NPC470265
0.7259	Intermediate Similarity	NPC23786
0.7239	Intermediate Similarity	NPC268530
0.7239	Intermediate Similarity	NPC4548
0.7239	Intermediate Similarity	NPC154491
0.7231	Intermediate Similarity	NPC470063
0.7231	Intermediate Similarity	NPC269530
0.7226	Intermediate Similarity	NPC473635
0.7214	Intermediate Similarity	NPC475139
0.7214	Intermediate Similarity	NPC180902
0.7209	Intermediate Similarity	NPC5103
0.7209	Intermediate Similarity	NPC477103
0.7206	Intermediate Similarity	NPC473979
0.7206	Intermediate Similarity	NPC469352
0.72	Intermediate Similarity	NPC137430
0.72	Intermediate Similarity	NPC162973
0.7197	Intermediate Similarity	NPC176840
0.7194	Intermediate Similarity	NPC175186
0.7194	Intermediate Similarity	NPC231529
0.7188	Intermediate Similarity	NPC469916
0.7188	Intermediate Similarity	NPC472439
0.7185	Intermediate Similarity	NPC159456
0.7185	Intermediate Similarity	NPC4021
0.7177	Intermediate Similarity	NPC470074
0.7177	Intermediate Similarity	NPC47024
0.7177	Intermediate Similarity	NPC474718
0.7176	Intermediate Similarity	NPC469496
0.7176	Intermediate Similarity	NPC106395
0.7176	Intermediate Similarity	NPC477126
0.7176	Intermediate Similarity	NPC469463
0.7176	Intermediate Similarity	NPC25909
0.7176	Intermediate Similarity	NPC469454
0.7176	Intermediate Similarity	NPC471204
0.7176	Intermediate Similarity	NPC46269
0.7164	Intermediate Similarity	NPC312536
0.7164	Intermediate Similarity	NPC470186
0.7162	Intermediate Similarity	NPC140021
0.7154	Intermediate Similarity	NPC317107
0.7154	Intermediate Similarity	NPC470076
0.7153	Intermediate Similarity	NPC8369
0.7143	Intermediate Similarity	NPC98249
0.7143	Intermediate Similarity	NPC8196
0.7143	Intermediate Similarity	NPC470493
0.7143	Intermediate Similarity	NPC284068
0.7143	Intermediate Similarity	NPC58662
0.7143	Intermediate Similarity	NPC53396
0.7143	Intermediate Similarity	NPC473968
0.7143	Intermediate Similarity	NPC312824
0.7143	Intermediate Similarity	NPC471170
0.7143	Intermediate Similarity	NPC120321
0.7143	Intermediate Similarity	NPC183580
0.7143	Intermediate Similarity	NPC13713
0.7143	Intermediate Similarity	NPC99266
0.7143	Intermediate Similarity	NPC61442
0.7132	Intermediate Similarity	NPC222688
0.7132	Intermediate Similarity	NPC477102
0.7132	Intermediate Similarity	NPC269642
0.7132	Intermediate Similarity	NPC475586
0.7132	Intermediate Similarity	NPC469370
0.7121	Intermediate Similarity	NPC133677
0.7121	Intermediate Similarity	NPC67290
0.7121	Intermediate Similarity	NPC238667
0.7121	Intermediate Similarity	NPC138303
0.712	Intermediate Similarity	NPC471412
0.7113	Intermediate Similarity	NPC473548
0.7113	Intermediate Similarity	NPC223356
0.7113	Intermediate Similarity	NPC471136
0.7113	Intermediate Similarity	NPC475500
0.7113	Intermediate Similarity	NPC100017
0.7113	Intermediate Similarity	NPC475154
0.7113	Intermediate Similarity	NPC476823
0.7113	Intermediate Similarity	NPC182266
0.7113	Intermediate Similarity	NPC471137
0.7111	Intermediate Similarity	NPC475003
0.7111	Intermediate Similarity	NPC48692
0.7111	Intermediate Similarity	NPC251226
0.7109	Intermediate Similarity	NPC180744
0.7101	Intermediate Similarity	NPC217901
0.7099	Intermediate Similarity	NPC234042
0.7099	Intermediate Similarity	NPC76550
0.7099	Intermediate Similarity	NPC152117
0.7099	Intermediate Similarity	NPC236217
0.7099	Intermediate Similarity	NPC123855
0.7099	Intermediate Similarity	NPC138757
0.7099	Intermediate Similarity	NPC317687
0.7097	Intermediate Similarity	NPC216478
0.709	Intermediate Similarity	NPC186525
0.709	Intermediate Similarity	NPC475372
0.709	Intermediate Similarity	NPC709

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 NPC476111 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	118
0.1-0.2	903
0.2-0.3	3266
0.3-0.4	3310
0.4-0.5	1169
0.5-0.6	337
0.6-0.7	44
0.7-0.8	3
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
0.7344	Intermediate Similarity	NPD6371	Approved
0.7185	Intermediate Similarity	NPD6909	Approved
0.7185	Intermediate Similarity	NPD6908	Approved
0.7015	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5344	Discontinued
0.6947	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6921	Approved
0.6853	Remote Similarity	NPD7260	Phase 2
0.6835	Remote Similarity	NPD7604	Phase 2
0.6772	Remote Similarity	NPD6648	Approved
0.6718	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7640	Approved
0.6641	Remote Similarity	NPD7639	Approved
0.6596	Remote Similarity	NPD7642	Approved
0.6575	Remote Similarity	NPD6845	Suspended
0.6575	Remote Similarity	NPD8338	Approved
0.6562	Remote Similarity	NPD7638	Approved
0.6554	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6686	Approved
0.6503	Remote Similarity	NPD7507	Approved
0.6483	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD8297	Approved
0.6429	Remote Similarity	NPD7516	Approved
0.6423	Remote Similarity	NPD4632	Approved
0.6418	Remote Similarity	NPD6899	Approved
0.6418	Remote Similarity	NPD6881	Approved
0.64	Remote Similarity	NPD46	Approved
0.64	Remote Similarity	NPD6698	Approved
0.6397	Remote Similarity	NPD6650	Approved
0.6397	Remote Similarity	NPD6649	Approved
0.6391	Remote Similarity	NPD6008	Approved
0.6391	Remote Similarity	NPD6402	Approved
0.6391	Remote Similarity	NPD7128	Approved
0.6391	Remote Similarity	NPD5739	Approved
0.6391	Remote Similarity	NPD6675	Approved
0.6383	Remote Similarity	NPD6319	Approved
0.6376	Remote Similarity	NPD8415	Approved
0.637	Remote Similarity	NPD6373	Approved
0.637	Remote Similarity	NPD6372	Approved
0.6357	Remote Similarity	NPD7328	Approved
0.6357	Remote Similarity	NPD7641	Discontinued
0.6357	Remote Similarity	NPD7327	Approved
0.635	Remote Similarity	NPD6053	Discontinued
0.6343	Remote Similarity	NPD5697	Approved
0.6343	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6883	Approved
0.6324	Remote Similarity	NPD7290	Approved
0.6324	Remote Similarity	NPD7102	Approved
0.6319	Remote Similarity	NPD7492	Approved
0.6301	Remote Similarity	NPD8336	Approved
0.6301	Remote Similarity	NPD8337	Approved
0.6296	Remote Similarity	NPD7320	Approved
0.6286	Remote Similarity	NPD6009	Approved
0.6277	Remote Similarity	NPD6847	Approved
0.6277	Remote Similarity	NPD6617	Approved
0.6277	Remote Similarity	NPD8130	Phase 1
0.6277	Remote Similarity	NPD6869	Approved
0.6276	Remote Similarity	NPD8451	Approved
0.6276	Remote Similarity	NPD6616	Approved
0.6268	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6013	Approved
0.625	Remote Similarity	NPD6014	Approved
0.6233	Remote Similarity	NPD8448	Approved
0.6233	Remote Similarity	NPD8074	Phase 3
0.6233	Remote Similarity	NPD7078	Approved
0.6232	Remote Similarity	NPD6882	Approved
0.6224	Remote Similarity	NPD5983	Phase 2
0.6222	Remote Similarity	NPD5701	Approved
0.6207	Remote Similarity	NPD8341	Approved
0.6207	Remote Similarity	NPD8340	Approved
0.6207	Remote Similarity	NPD8342	Approved
0.6207	Remote Similarity	NPD8299	Approved
0.619	Remote Similarity	NPD7736	Approved
0.6181	Remote Similarity	NPD6370	Approved
0.6176	Remote Similarity	NPD6011	Approved
0.6172	Remote Similarity	NPD6399	Phase 3
0.6165	Remote Similarity	NPD5211	Phase 2
0.6165	Remote Similarity	NPD7632	Discontinued
0.6164	Remote Similarity	NPD6336	Discontinued
0.6164	Remote Similarity	NPD8273	Phase 1
0.6154	Remote Similarity	NPD6059	Approved
0.6144	Remote Similarity	NPD6333	Approved
0.6144	Remote Similarity	NPD6334	Approved
0.6138	Remote Similarity	NPD7122	Discontinued
0.6122	Remote Similarity	NPD8293	Discontinued
0.6111	Remote Similarity	NPD8378	Approved
0.6111	Remote Similarity	NPD8033	Approved
0.6111	Remote Similarity	NPD6015	Approved
0.6111	Remote Similarity	NPD8296	Approved
0.6111	Remote Similarity	NPD6016	Approved
0.6111	Remote Similarity	NPD8380	Approved
0.6111	Remote Similarity	NPD8335	Approved
0.6111	Remote Similarity	NPD8379	Approved
0.6107	Remote Similarity	NPD8392	Approved
0.6107	Remote Similarity	NPD7902	Approved
0.6107	Remote Similarity	NPD8390	Approved
0.6107	Remote Similarity	NPD8391	Approved
0.6087	Remote Similarity	NPD6421	Discontinued
0.6074	Remote Similarity	NPD5141	Approved
0.6069	Remote Similarity	NPD5988	Approved
0.6063	Remote Similarity	NPD1695	Approved
0.6043	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8377	Approved
0.6042	Remote Similarity	NPD8294	Approved
0.6029	Remote Similarity	NPD5357	Phase 1
0.6027	Remote Similarity	NPD8328	Phase 3
0.6016	Remote Similarity	NPD7838	Discovery
0.6016	Remote Similarity	NPD3168	Discontinued
0.6016	Remote Similarity	NPD5785	Approved
0.6015	Remote Similarity	NPD5285	Approved
0.6015	Remote Similarity	NPD4696	Approved
0.6015	Remote Similarity	NPD5286	Approved
0.6014	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD1694	Approved
0.6	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.5986	Remote Similarity	NPD6274	Approved
0.5985	Remote Similarity	NPD4755	Approved
0.5985	Remote Similarity	NPD6083	Phase 2
0.5985	Remote Similarity	NPD6412	Phase 2
0.5985	Remote Similarity	NPD6084	Phase 2
0.5972	Remote Similarity	NPD7100	Approved
0.5972	Remote Similarity	NPD7101	Approved
0.5971	Remote Similarity	NPD4634	Approved
0.5969	Remote Similarity	NPD6079	Approved
0.5969	Remote Similarity	NPD7515	Phase 2
0.5959	Remote Similarity	NPD8080	Discontinued
0.5957	Remote Similarity	NPD1376	Discontinued
0.5957	Remote Similarity	NPD8133	Approved
0.5954	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD7500	Approved
0.594	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5328	Approved
0.5932	Remote Similarity	NPD8368	Discontinued
0.5929	Remote Similarity	NPD2204	Approved
0.5926	Remote Similarity	NPD5226	Approved
0.5926	Remote Similarity	NPD5224	Approved
0.5926	Remote Similarity	NPD5225	Approved
0.5926	Remote Similarity	NPD4633	Approved
0.5924	Remote Similarity	NPD8384	Approved
0.5923	Remote Similarity	NPD5778	Approved
0.5923	Remote Similarity	NPD5779	Approved
0.5922	Remote Similarity	NPD8407	Phase 2
0.5918	Remote Similarity	NPD7830	Approved
0.5918	Remote Similarity	NPD7829	Approved
0.5903	Remote Similarity	NPD6335	Approved
0.5896	Remote Similarity	NPD4700	Approved
0.5894	Remote Similarity	NPD6914	Discontinued
0.5887	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5174	Approved
0.5882	Remote Similarity	NPD5175	Approved
0.5878	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD7900	Approved
0.5878	Remote Similarity	NPD5282	Discontinued
0.5873	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD1696	Phase 3
0.5852	Remote Similarity	NPD5223	Approved
0.5846	Remote Similarity	NPD7637	Suspended
0.5846	Remote Similarity	NPD7983	Approved
0.5839	Remote Similarity	NPD7625	Phase 1
0.5833	Remote Similarity	NPD6317	Approved
0.5833	Remote Similarity	NPD5695	Phase 3
0.5833	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD3618	Phase 1
0.5821	Remote Similarity	NPD5696	Approved
0.5816	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD4202	Approved
0.5797	Remote Similarity	NPD6640	Phase 3
0.5793	Remote Similarity	NPD6314	Approved
0.5793	Remote Similarity	NPD6313	Approved
0.5792	Remote Similarity	NPD8360	Approved
0.5792	Remote Similarity	NPD8361	Approved
0.5789	Remote Similarity	NPD5222	Approved
0.5789	Remote Similarity	NPD4697	Phase 3
0.5789	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5221	Approved
0.5782	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD7524	Approved
0.5778	Remote Similarity	NPD6404	Discontinued
0.5769	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD6868	Approved
0.5763	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD6033	Approved
0.5746	Remote Similarity	NPD5173	Approved
0.5743	Remote Similarity	NPD7623	Phase 3
0.5743	Remote Similarity	NPD7624	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