NPASS Compound

Structure

NPC90814 OpenBabel07101718302D 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 2 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 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 14 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:	517.3
Volume:	535.26
LogP:	3.119
LogD:	1.56
LogS:	-4.234
# Rotatable Bonds:	8
TPSA:	113.37
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	5.366
Fsp3:	0.759
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:	-5.242
MDCK Permeability:	6.0054080677218735e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.083
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.329

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	27.659984588623047%
Volume Distribution (VD):	1.272
Pgp-substrate:	73.18270874023438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.497
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	5.205
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.75
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.612
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.213
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC90814

Natural Product ID:	NPC90814
*Common Name:**	VCEYVQJHAJGATA-MBCQSGEESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VCEYVQJHAJGATA-MBCQSGEESA-N
Standard InCHI:	InChI=1S/C29H43NO7/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/h10,12,14,16,19-22,24-25,31,35H,11,13H2,1-9H3/t16-,19-,20-,21+,22-,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@H](N(C)C)C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500387
PubChem CID:	11649268
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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	1.0	nM	PMID[528935]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	2200.0	nM	PMID[528935]

☑ 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 NPC90814 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	132
0.1-0.2	894
0.2-0.3	3521
0.3-0.4	10899
0.4-0.5	15611
0.5-0.6	9073
0.6-0.7	2382
0.7-0.8	113
0.8-0.85	55
0.85-0.9	13
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189393
0.9677	High Similarity	NPC243902
0.9435	High Similarity	NPC476111
0.8667	High Similarity	NPC472757
0.8595	High Similarity	NPC472400
0.8525	High Similarity	NPC471127
0.8525	High Similarity	NPC154363
0.8525	High Similarity	NPC234858
0.8455	Intermediate Similarity	NPC10721
0.8387	Intermediate Similarity	NPC472758
0.8387	Intermediate Similarity	NPC472397
0.8387	Intermediate Similarity	NPC471125
0.8387	Intermediate Similarity	NPC171905
0.832	Intermediate Similarity	NPC471108
0.832	Intermediate Similarity	NPC236918
0.832	Intermediate Similarity	NPC156745
0.832	Intermediate Similarity	NPC22628
0.832	Intermediate Similarity	NPC5989
0.832	Intermediate Similarity	NPC255081
0.832	Intermediate Similarity	NPC275696
0.832	Intermediate Similarity	NPC5991
0.8306	Intermediate Similarity	NPC156252
0.8254	Intermediate Similarity	NPC145182
0.8254	Intermediate Similarity	NPC471128
0.8254	Intermediate Similarity	NPC157252
0.8254	Intermediate Similarity	NPC329080
0.8254	Intermediate Similarity	NPC475885
0.8254	Intermediate Similarity	NPC472759
0.8254	Intermediate Similarity	NPC471126
0.824	Intermediate Similarity	NPC146280
0.824	Intermediate Similarity	NPC124676
0.8189	Intermediate Similarity	NPC52839
0.8189	Intermediate Similarity	NPC472401
0.8125	Intermediate Similarity	NPC19464
0.8062	Intermediate Similarity	NPC472399
0.8049	Intermediate Similarity	NPC475937
0.8049	Intermediate Similarity	NPC158523
0.8	Intermediate Similarity	NPC145238
0.7984	Intermediate Similarity	NPC162009
0.7984	Intermediate Similarity	NPC257017
0.7967	Intermediate Similarity	NPC153036
0.792	Intermediate Similarity	NPC71889
0.7857	Intermediate Similarity	NPC474872
0.776	Intermediate Similarity	NPC260786
0.776	Intermediate Similarity	NPC174471
0.776	Intermediate Similarity	NPC96739
0.776	Intermediate Similarity	NPC474871
0.7744	Intermediate Similarity	NPC204556
0.7742	Intermediate Similarity	NPC163004
0.7734	Intermediate Similarity	NPC153651
0.7698	Intermediate Similarity	NPC151216
0.7698	Intermediate Similarity	NPC170212
0.7698	Intermediate Similarity	NPC215643
0.7698	Intermediate Similarity	NPC101825
0.7698	Intermediate Similarity	NPC475391
0.7698	Intermediate Similarity	NPC265499
0.7698	Intermediate Similarity	NPC17138
0.7698	Intermediate Similarity	NPC89227
0.7698	Intermediate Similarity	NPC221511
0.7692	Intermediate Similarity	NPC185876
0.7692	Intermediate Similarity	NPC19336
0.7687	Intermediate Similarity	NPC270109
0.7674	Intermediate Similarity	NPC472760
0.7638	Intermediate Similarity	NPC477091
0.7638	Intermediate Similarity	NPC474937
0.7615	Intermediate Similarity	NPC180640
0.7538	Intermediate Similarity	NPC9714
0.7537	Intermediate Similarity	NPC222307
0.7481	Intermediate Similarity	NPC472667
0.7463	Intermediate Similarity	NPC473919
0.7463	Intermediate Similarity	NPC473709
0.746	Intermediate Similarity	NPC273433
0.7422	Intermediate Similarity	NPC472002
0.7388	Intermediate Similarity	NPC473802
0.7385	Intermediate Similarity	NPC179626
0.7376	Intermediate Similarity	NPC246209
0.7353	Intermediate Similarity	NPC471940
0.7323	Intermediate Similarity	NPC218602
0.7302	Intermediate Similarity	NPC187435
0.7302	Intermediate Similarity	NPC67321
0.7299	Intermediate Similarity	NPC236999
0.7293	Intermediate Similarity	NPC143755
0.7279	Intermediate Similarity	NPC293112
0.7279	Intermediate Similarity	NPC471939
0.7239	Intermediate Similarity	NPC310511
0.7236	Intermediate Similarity	NPC470074
0.7209	Intermediate Similarity	NPC474846
0.7209	Intermediate Similarity	NPC469656
0.7209	Intermediate Similarity	NPC469655
0.7203	Intermediate Similarity	NPC476558
0.7197	Intermediate Similarity	NPC469684
0.7185	Intermediate Similarity	NPC222688
0.7174	Intermediate Similarity	NPC470850
0.7165	Intermediate Similarity	NPC143609
0.7154	Intermediate Similarity	NPC234042
0.7154	Intermediate Similarity	NPC152117
0.7143	Intermediate Similarity	NPC251310
0.7132	Intermediate Similarity	NPC469789
0.7132	Intermediate Similarity	NPC253906
0.7132	Intermediate Similarity	NPC11895
0.7132	Intermediate Similarity	NPC257240
0.7122	Intermediate Similarity	NPC104382
0.7122	Intermediate Similarity	NPC470851
0.7121	Intermediate Similarity	NPC471816
0.7121	Intermediate Similarity	NPC470793
0.712	Intermediate Similarity	NPC476081
0.7111	Intermediate Similarity	NPC67569
0.7109	Intermediate Similarity	NPC306265
0.7099	Intermediate Similarity	NPC317210
0.7099	Intermediate Similarity	NPC250109
0.7099	Intermediate Similarity	NPC962
0.709	Intermediate Similarity	NPC475041
0.709	Intermediate Similarity	NPC469380
0.7087	Intermediate Similarity	NPC111952
0.708	Intermediate Similarity	NPC81736
0.708	Intermediate Similarity	NPC172154
0.7077	Intermediate Similarity	NPC188738
0.7068	Intermediate Similarity	NPC473656
0.7068	Intermediate Similarity	NPC475323
0.7063	Intermediate Similarity	NPC478057
0.7059	Intermediate Similarity	NPC23786
0.7059	Intermediate Similarity	NPC170538
0.7059	Intermediate Similarity	NPC470265
0.7045	Intermediate Similarity	NPC117712
0.7045	Intermediate Similarity	NPC473798
0.704	Intermediate Similarity	NPC97435
0.7037	Intermediate Similarity	NPC4548
0.7037	Intermediate Similarity	NPC154491
0.7037	Intermediate Similarity	NPC268530
0.7031	Intermediate Similarity	NPC230541
0.7029	Intermediate Similarity	NPC473635
0.7023	Intermediate Similarity	NPC269530
0.7023	Intermediate Similarity	NPC474516
0.7023	Intermediate Similarity	NPC470063
0.7021	Intermediate Similarity	NPC475139
0.7021	Intermediate Similarity	NPC180902
0.7007	Intermediate Similarity	NPC473979
0.7007	Intermediate Similarity	NPC469352
0.7	Intermediate Similarity	NPC175186
0.7	Intermediate Similarity	NPC231529
0.7	Intermediate Similarity	NPC477103
0.7	Intermediate Similarity	NPC5103
0.6992	Remote Similarity	NPC96312
0.6992	Remote Similarity	NPC40632
0.6992	Remote Similarity	NPC251236
0.6992	Remote Similarity	NPC49492
0.6992	Remote Similarity	NPC328374
0.6992	Remote Similarity	NPC266728
0.6992	Remote Similarity	NPC30196
0.6992	Remote Similarity	NPC176840
0.6992	Remote Similarity	NPC474734
0.6985	Remote Similarity	NPC4021
0.6985	Remote Similarity	NPC159456
0.6985	Remote Similarity	NPC242692
0.6984	Remote Similarity	NPC136289
0.6984	Remote Similarity	NPC162973
0.6984	Remote Similarity	NPC137430
0.698	Remote Similarity	NPC140021
0.6977	Remote Similarity	NPC472219
0.6977	Remote Similarity	NPC472217
0.6977	Remote Similarity	NPC472439
0.6977	Remote Similarity	NPC472218
0.6977	Remote Similarity	NPC469916
0.6977	Remote Similarity	NPC102843
0.697	Remote Similarity	NPC25909
0.697	Remote Similarity	NPC469463
0.697	Remote Similarity	NPC469454
0.697	Remote Similarity	NPC46269
0.697	Remote Similarity	NPC49451
0.697	Remote Similarity	NPC106395
0.697	Remote Similarity	NPC474271
0.697	Remote Similarity	NPC477126
0.697	Remote Similarity	NPC469496
0.697	Remote Similarity	NPC471204
0.6963	Remote Similarity	NPC470186
0.6963	Remote Similarity	NPC312536
0.696	Remote Similarity	NPC306856
0.696	Remote Similarity	NPC474718
0.696	Remote Similarity	NPC47024
0.696	Remote Similarity	NPC476274
0.6957	Remote Similarity	NPC8369
0.6953	Remote Similarity	NPC102352
0.6953	Remote Similarity	NPC323834
0.6953	Remote Similarity	NPC60315
0.695	Remote Similarity	NPC471170
0.6947	Remote Similarity	NPC317107
0.6947	Remote Similarity	NPC474229
0.6947	Remote Similarity	NPC470076
0.694	Remote Similarity	NPC98249
0.694	Remote Similarity	NPC176513
0.694	Remote Similarity	NPC312824
0.694	Remote Similarity	NPC6531
0.694	Remote Similarity	NPC470854
0.694	Remote Similarity	NPC473968
0.694	Remote Similarity	NPC97908
0.694	Remote Similarity	NPC284068
0.694	Remote Similarity	NPC470775
0.694	Remote Similarity	NPC474654
0.694	Remote Similarity	NPC53396
0.694	Remote Similarity	NPC13713

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 NPC90814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	113
0.1-0.2	872
0.2-0.3	3250
0.3-0.4	3239
0.4-0.5	1232
0.5-0.6	385
0.6-0.7	58
0.7-0.8	1
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
0.7368	Intermediate Similarity	NPD6909	Approved
0.7368	Intermediate Similarity	NPD6908	Approved
0.7132	Intermediate Similarity	NPD6371	Approved
0.6985	Remote Similarity	NPD6921	Approved
0.6972	Remote Similarity	NPD8338	Approved
0.6884	Remote Similarity	NPD7604	Phase 2
0.6815	Remote Similarity	NPD7115	Discovery
0.6794	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5344	Discontinued
0.6765	Remote Similarity	NPD7641	Discontinued
0.6763	Remote Similarity	NPD7642	Approved
0.6742	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.669	Remote Similarity	NPD8336	Approved
0.669	Remote Similarity	NPD8337	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6596	Remote Similarity	NPD8341	Approved
0.6596	Remote Similarity	NPD8299	Approved
0.6596	Remote Similarity	NPD8340	Approved
0.6596	Remote Similarity	NPD8342	Approved
0.6562	Remote Similarity	NPD6648	Approved
0.6531	Remote Similarity	NPD8415	Approved
0.6519	Remote Similarity	NPD8297	Approved
0.6515	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6845	Suspended
0.6484	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD4632	Approved
0.6466	Remote Similarity	NPD6899	Approved
0.6466	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6881	Approved
0.6444	Remote Similarity	NPD6650	Approved
0.6444	Remote Similarity	NPD6649	Approved
0.6439	Remote Similarity	NPD6402	Approved
0.6439	Remote Similarity	NPD6008	Approved
0.6439	Remote Similarity	NPD5739	Approved
0.6439	Remote Similarity	NPD7128	Approved
0.6439	Remote Similarity	NPD6675	Approved
0.6434	Remote Similarity	NPD7640	Approved
0.6434	Remote Similarity	NPD8451	Approved
0.6434	Remote Similarity	NPD7639	Approved
0.6429	Remote Similarity	NPD6319	Approved
0.6418	Remote Similarity	NPD6372	Approved
0.6418	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD7122	Discontinued
0.6391	Remote Similarity	NPD5697	Approved
0.6389	Remote Similarity	NPD8448	Approved
0.637	Remote Similarity	NPD7290	Approved
0.637	Remote Similarity	NPD6883	Approved
0.637	Remote Similarity	NPD6421	Discontinued
0.637	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD7492	Approved
0.6357	Remote Similarity	NPD7638	Approved
0.6343	Remote Similarity	NPD6686	Approved
0.6343	Remote Similarity	NPD7320	Approved
0.6338	Remote Similarity	NPD8080	Discontinued
0.6331	Remote Similarity	NPD6009	Approved
0.6324	Remote Similarity	NPD6869	Approved
0.6324	Remote Similarity	NPD8130	Phase 1
0.6324	Remote Similarity	NPD6617	Approved
0.6324	Remote Similarity	NPD6847	Approved
0.6319	Remote Similarity	NPD8273	Phase 1
0.6319	Remote Similarity	NPD7507	Approved
0.6319	Remote Similarity	NPD6616	Approved
0.6316	Remote Similarity	NPD5357	Phase 1
0.6312	Remote Similarity	NPD6054	Approved
0.6301	Remote Similarity	NPD7319	Approved
0.6296	Remote Similarity	NPD6014	Approved
0.6296	Remote Similarity	NPD6013	Approved
0.6296	Remote Similarity	NPD6012	Approved
0.6277	Remote Similarity	NPD6882	Approved
0.6276	Remote Similarity	NPD7078	Approved
0.6269	Remote Similarity	NPD5701	Approved
0.6268	Remote Similarity	NPD5983	Phase 2
0.6259	Remote Similarity	NPD8392	Approved
0.6259	Remote Similarity	NPD8391	Approved
0.6259	Remote Similarity	NPD8390	Approved
0.6241	Remote Similarity	NPD7516	Approved
0.6233	Remote Similarity	NPD7736	Approved
0.6224	Remote Similarity	NPD6370	Approved
0.6222	Remote Similarity	NPD6011	Approved
0.622	Remote Similarity	NPD6399	Phase 3
0.6214	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5211	Phase 2
0.6207	Remote Similarity	NPD6336	Discontinued
0.6197	Remote Similarity	NPD6059	Approved
0.619	Remote Similarity	NPD6698	Approved
0.619	Remote Similarity	NPD46	Approved
0.6184	Remote Similarity	NPD6333	Approved
0.6184	Remote Similarity	NPD6334	Approved
0.617	Remote Similarity	NPD7328	Approved
0.617	Remote Similarity	NPD7327	Approved
0.6164	Remote Similarity	NPD8293	Discontinued
0.6159	Remote Similarity	NPD6053	Discontinued
0.6154	Remote Similarity	NPD6016	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6015	Approved
0.6149	Remote Similarity	NPD6914	Discontinued
0.6148	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5141	Approved
0.6111	Remote Similarity	NPD5988	Approved
0.6087	Remote Similarity	NPD2204	Approved
0.6087	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD8328	Phase 3
0.6065	Remote Similarity	NPD8384	Approved
0.6063	Remote Similarity	NPD3168	Discontinued
0.6061	Remote Similarity	NPD5286	Approved
0.6061	Remote Similarity	NPD5285	Approved
0.6061	Remote Similarity	NPD4696	Approved
0.6058	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD8074	Phase 3
0.6047	Remote Similarity	NPD7748	Approved
0.6031	Remote Similarity	NPD6084	Phase 2
0.6031	Remote Similarity	NPD4755	Approved
0.6031	Remote Similarity	NPD6083	Phase 2
0.6029	Remote Similarity	NPD6412	Phase 2
0.6028	Remote Similarity	NPD6274	Approved
0.6016	Remote Similarity	NPD6079	Approved
0.6016	Remote Similarity	NPD7515	Phase 2
0.6014	Remote Similarity	NPD4634	Approved
0.6014	Remote Similarity	NPD7100	Approved
0.6014	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5328	Approved
0.597	Remote Similarity	NPD5225	Approved
0.597	Remote Similarity	NPD5226	Approved
0.597	Remote Similarity	NPD4633	Approved
0.597	Remote Similarity	NPD5224	Approved
0.597	Remote Similarity	NPD7632	Discontinued
0.5969	Remote Similarity	NPD5779	Approved
0.5969	Remote Similarity	NPD5778	Approved
0.5966	Remote Similarity	NPD8368	Discontinued
0.5959	Remote Similarity	NPD7829	Approved
0.5959	Remote Similarity	NPD7830	Approved
0.5956	Remote Similarity	NPD7333	Discontinued
0.5955	Remote Similarity	NPD8407	Phase 2
0.5954	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD6335	Approved
0.594	Remote Similarity	NPD4700	Approved
0.5931	Remote Similarity	NPD8380	Approved
0.5931	Remote Similarity	NPD8379	Approved
0.5931	Remote Similarity	NPD8033	Approved
0.5931	Remote Similarity	NPD8296	Approved
0.5931	Remote Similarity	NPD8335	Approved
0.5931	Remote Similarity	NPD8378	Approved
0.5926	Remote Similarity	NPD5175	Approved
0.5926	Remote Similarity	NPD5174	Approved
0.5923	Remote Similarity	NPD5282	Discontinued
0.5923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD7900	Approved
0.592	Remote Similarity	NPD1696	Phase 3
0.5903	Remote Similarity	NPD7519	Approved
0.5903	Remote Similarity	NPD7517	Approved
0.5903	Remote Similarity	NPD7518	Approved
0.5896	Remote Similarity	NPD5223	Approved
0.5891	Remote Similarity	NPD7983	Approved
0.5891	Remote Similarity	NPD7637	Suspended
0.5887	Remote Similarity	NPD1376	Discontinued
0.5878	Remote Similarity	NPD5695	Phase 3
0.5874	Remote Similarity	NPD6317	Approved
0.5873	Remote Similarity	NPD3618	Phase 1
0.5865	Remote Similarity	NPD5696	Approved
0.5862	Remote Similarity	NPD8377	Approved
0.5862	Remote Similarity	NPD8294	Approved
0.5859	Remote Similarity	NPD1695	Approved
0.5852	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD4202	Approved
0.5839	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6314	Approved
0.5833	Remote Similarity	NPD5222	Approved
0.5833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4697	Phase 3
0.5833	Remote Similarity	NPD6313	Approved
0.5833	Remote Similarity	NPD5221	Approved
0.5827	Remote Similarity	NPD7524	Approved
0.5824	Remote Similarity	NPD8361	Approved
0.5824	Remote Similarity	NPD8360	Approved
0.5822	Remote Similarity	NPD8513	Phase 3
0.5822	Remote Similarity	NPD8516	Approved
0.5822	Remote Similarity	NPD7503	Approved
0.5822	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD8515	Approved
0.5822	Remote Similarity	NPD8517	Approved
0.5821	Remote Similarity	NPD6404	Discontinued
0.5814	Remote Similarity	NPD5785	Approved
0.5814	Remote Similarity	NPD7838	Discovery
0.5809	Remote Similarity	NPD8275	Approved
0.5809	Remote Similarity	NPD8276	Approved
0.5804	Remote Similarity	NPD6868	Approved
0.5801	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6033	Approved
0.5795	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD1694	Approved
0.5789	Remote Similarity	NPD5173	Approved
0.5776	Remote Similarity	NPD2575	Approved
0.5775	Remote Similarity	NPD8133	Approved
0.5769	Remote Similarity	NPD8034	Phase 2
0.5769	Remote Similarity	NPD8035	Phase 2
0.5764	Remote Similarity	NPD8295	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