NPASS Compound

Structure

CID266957 OpenBabel06191716072D 29 31 0 0 1 0 0 0 0 0999 V2000 0.1082 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 4.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8279 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0592 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6470 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6470 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0592 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 5.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.7361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 4.7361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8970 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.7361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 11 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 14 29 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 26 1 6 0 0 0 17 19 1 0 0 0 0 17 28 1 6 0 0 0 18 10 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 19 13 1 6 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	409.112
LogP:	2.321
LogD:	2.563
LogS:	-3.81
# Rotatable Bonds:	5
TPSA:	91.43
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	5.166
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.948
MDCK Permeability:	9.681312803877518e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.944
20% Bioavailability (F20%):	0.566
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.216
Plasma Protein Binding (PPB):	84.64910125732422%
Volume Distribution (VD):	0.991
Pgp-substrate:	14.465822219848633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.503
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.597
CYP3A4-substrate:	0.33

ADMET: Excretion

Clearance (CL):	8.882
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.811
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.802
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.54
Carcinogencity:	0.138
Eye Corrosion:	0.006
Eye Irritation:	0.018
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC266957

Natural Product ID:	NPC266957
*Common Name:**	Ursiniolide A
IUPAC Name:	[(3aR,4R,6E,9S,10E,11aS)-9-acetyloxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2,3-dimethyloxirane-2-carboxylate
Synonyms:
Standard InCHIKey:	XBYFQUZGOAYUQG-DMPWRENPSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-11-7-8-16(26-15(5)23)12(2)10-18-19(13(3)20(24)27-18)17(9-11)28-21(25)22(6)14(4)29-22/h7,10,14,16-19H,3,8-9H2,1-2,4-6H3/b11-7+,12-10+/t14?,16-,17+,18-,19+,22?/m0/s1
SMILES:	C/C/1=CC[C@@H](/C(=C/[C@H]2[C@H](C(=C)C(=O)O2)[C@@H](C1)OC(=O)C1(C)C(C)O1)/C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL270551
PubChem CID:	44457227
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4307	Canarium album	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4307	Canarium album	Species	Burseraceae	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
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	1780.0	nM	PMID[529875]

☑ 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 NPC266957 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	234
0.1-0.2	1679
0.2-0.3	6765
0.3-0.4	15790
0.4-0.5	10179
0.5-0.6	5443
0.6-0.7	2009
0.7-0.8	476
0.8-0.85	97
0.85-0.9	21
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC165383
0.9101	High Similarity	NPC17585
0.9	High Similarity	NPC471140
0.8804	High Similarity	NPC475949
0.8804	High Similarity	NPC477512
0.8765	High Similarity	NPC476028
0.8765	High Similarity	NPC171204
0.8765	High Similarity	NPC141789
0.8736	High Similarity	NPC287089
0.871	High Similarity	NPC164598
0.871	High Similarity	NPC264477
0.871	High Similarity	NPC474339
0.871	High Similarity	NPC477511
0.8667	High Similarity	NPC471147
0.8617	High Similarity	NPC471148
0.8571	High Similarity	NPC475659
0.8571	High Similarity	NPC141810
0.8554	High Similarity	NPC270126
0.8523	High Similarity	NPC475902
0.8506	High Similarity	NPC469910
0.8506	High Similarity	NPC50637
0.8488	Intermediate Similarity	NPC158756
0.8478	Intermediate Similarity	NPC473859
0.8452	Intermediate Similarity	NPC281132
0.8444	Intermediate Similarity	NPC20713
0.8438	Intermediate Similarity	NPC477510
0.8438	Intermediate Similarity	NPC471143
0.8427	Intermediate Similarity	NPC151770
0.8391	Intermediate Similarity	NPC470755
0.8372	Intermediate Similarity	NPC474703
0.8333	Intermediate Similarity	NPC474232
0.8333	Intermediate Similarity	NPC617
0.8315	Intermediate Similarity	NPC476803
0.8313	Intermediate Similarity	NPC97516
0.8313	Intermediate Similarity	NPC474760
0.8298	Intermediate Similarity	NPC471144
0.8272	Intermediate Similarity	NPC269206
0.8272	Intermediate Similarity	NPC58956
0.8272	Intermediate Similarity	NPC295633
0.8265	Intermediate Similarity	NPC477513
0.8261	Intermediate Similarity	NPC473330
0.8261	Intermediate Similarity	NPC140543
0.8261	Intermediate Similarity	NPC473316
0.8222	Intermediate Similarity	NPC475971
0.8222	Intermediate Similarity	NPC166919
0.8211	Intermediate Similarity	NPC288876
0.8202	Intermediate Similarity	NPC231889
0.8182	Intermediate Similarity	NPC38468
0.8182	Intermediate Similarity	NPC319795
0.8182	Intermediate Similarity	NPC50362
0.8171	Intermediate Similarity	NPC476355
0.8171	Intermediate Similarity	NPC140287
0.8161	Intermediate Similarity	NPC473390
0.8161	Intermediate Similarity	NPC40746
0.8161	Intermediate Similarity	NPC169575
0.8161	Intermediate Similarity	NPC131669
0.8161	Intermediate Similarity	NPC475947
0.8152	Intermediate Similarity	NPC475302
0.8148	Intermediate Similarity	NPC163003
0.8144	Intermediate Similarity	NPC19239
0.8144	Intermediate Similarity	NPC474166
0.814	Intermediate Similarity	NPC24417
0.8132	Intermediate Similarity	NPC475748
0.8125	Intermediate Similarity	NPC201718
0.8118	Intermediate Similarity	NPC98557
0.8118	Intermediate Similarity	NPC167881
0.8111	Intermediate Similarity	NPC476805
0.8111	Intermediate Similarity	NPC475819
0.8105	Intermediate Similarity	NPC208233
0.809	Intermediate Similarity	NPC38576
0.809	Intermediate Similarity	NPC279859
0.8085	Intermediate Similarity	NPC230800
0.8085	Intermediate Similarity	NPC279621
0.8085	Intermediate Similarity	NPC35498
0.8068	Intermediate Similarity	NPC476804
0.8065	Intermediate Similarity	NPC57405
0.8065	Intermediate Similarity	NPC476267
0.8065	Intermediate Similarity	NPC121825
0.8065	Intermediate Similarity	NPC303942
0.8046	Intermediate Similarity	NPC475690
0.8046	Intermediate Similarity	NPC229825
0.8041	Intermediate Similarity	NPC149371
0.798	Intermediate Similarity	NPC9303
0.798	Intermediate Similarity	NPC16313
0.798	Intermediate Similarity	NPC475802
0.7979	Intermediate Similarity	NPC477922
0.7979	Intermediate Similarity	NPC471142
0.7978	Intermediate Similarity	NPC255307
0.7976	Intermediate Similarity	NPC235906
0.7976	Intermediate Similarity	NPC123360
0.7957	Intermediate Similarity	NPC469692
0.7957	Intermediate Similarity	NPC469645
0.7957	Intermediate Similarity	NPC125674
0.7957	Intermediate Similarity	NPC228451
0.7957	Intermediate Similarity	NPC475838
0.7955	Intermediate Similarity	NPC59097
0.7938	Intermediate Similarity	NPC185141
0.7938	Intermediate Similarity	NPC47880
0.7938	Intermediate Similarity	NPC110443
0.7938	Intermediate Similarity	NPC128733
0.7938	Intermediate Similarity	NPC46998
0.7938	Intermediate Similarity	NPC133907
0.7935	Intermediate Similarity	NPC473619
0.7935	Intermediate Similarity	NPC251385
0.7935	Intermediate Similarity	NPC469718
0.7935	Intermediate Similarity	NPC49342
0.7935	Intermediate Similarity	NPC329857
0.7931	Intermediate Similarity	NPC301477
0.7931	Intermediate Similarity	NPC79277
0.7931	Intermediate Similarity	NPC475481
0.7931	Intermediate Similarity	NPC25684
0.7931	Intermediate Similarity	NPC281949
0.7917	Intermediate Similarity	NPC279561
0.7912	Intermediate Similarity	NPC475906
0.7912	Intermediate Similarity	NPC469628
0.7912	Intermediate Similarity	NPC471047
0.7912	Intermediate Similarity	NPC469631
0.7912	Intermediate Similarity	NPC469653
0.7907	Intermediate Similarity	NPC473980
0.7907	Intermediate Similarity	NPC473981
0.79	Intermediate Similarity	NPC324327
0.79	Intermediate Similarity	NPC474421
0.79	Intermediate Similarity	NPC475510
0.79	Intermediate Similarity	NPC194620
0.79	Intermediate Similarity	NPC72813
0.79	Intermediate Similarity	NPC475587
0.79	Intermediate Similarity	NPC326994
0.7895	Intermediate Similarity	NPC477921
0.7895	Intermediate Similarity	NPC476275
0.7889	Intermediate Similarity	NPC305475
0.7889	Intermediate Similarity	NPC475461
0.7889	Intermediate Similarity	NPC469483
0.7879	Intermediate Similarity	NPC474741
0.7872	Intermediate Similarity	NPC474247
0.7865	Intermediate Similarity	NPC114979
0.7865	Intermediate Similarity	NPC96259
0.7865	Intermediate Similarity	NPC191476
0.7865	Intermediate Similarity	NPC141193
0.7857	Intermediate Similarity	NPC155587
0.7849	Intermediate Similarity	NPC473321
0.7822	Intermediate Similarity	NPC14862
0.7822	Intermediate Similarity	NPC474664
0.7822	Intermediate Similarity	NPC327286
0.7822	Intermediate Similarity	NPC169888
0.7822	Intermediate Similarity	NPC473939
0.7822	Intermediate Similarity	NPC233379
0.7822	Intermediate Similarity	NPC55972
0.7822	Intermediate Similarity	NPC473595
0.7802	Intermediate Similarity	NPC471739
0.7791	Intermediate Similarity	NPC108816
0.7791	Intermediate Similarity	NPC475699
0.7791	Intermediate Similarity	NPC471465
0.7791	Intermediate Similarity	NPC267231
0.7791	Intermediate Similarity	NPC196653
0.7791	Intermediate Similarity	NPC93763
0.7789	Intermediate Similarity	NPC471141
0.7789	Intermediate Similarity	NPC474947
0.7789	Intermediate Similarity	NPC270013
0.7789	Intermediate Similarity	NPC14961
0.7766	Intermediate Similarity	NPC273579
0.7766	Intermediate Similarity	NPC162205
0.7766	Intermediate Similarity	NPC212486
0.7766	Intermediate Similarity	NPC295204
0.7766	Intermediate Similarity	NPC288240
0.7755	Intermediate Similarity	NPC476270
0.7753	Intermediate Similarity	NPC318468
0.7753	Intermediate Similarity	NPC475989
0.7753	Intermediate Similarity	NPC272814
0.7753	Intermediate Similarity	NPC128429
0.7753	Intermediate Similarity	NPC170286
0.7745	Intermediate Similarity	NPC475922
0.7745	Intermediate Similarity	NPC15218
0.7742	Intermediate Similarity	NPC469368
0.7742	Intermediate Similarity	NPC51653
0.7742	Intermediate Similarity	NPC179394
0.7742	Intermediate Similarity	NPC312042
0.7742	Intermediate Similarity	NPC475855
0.7742	Intermediate Similarity	NPC144133
0.7732	Intermediate Similarity	NPC473326
0.7727	Intermediate Similarity	NPC286229
0.7727	Intermediate Similarity	NPC52861
0.7717	Intermediate Similarity	NPC473715
0.7711	Intermediate Similarity	NPC129665
0.7708	Intermediate Similarity	NPC476315
0.7701	Intermediate Similarity	NPC178277
0.7692	Intermediate Similarity	NPC150755
0.7692	Intermediate Similarity	NPC204048
0.7684	Intermediate Similarity	NPC474035
0.7684	Intermediate Similarity	NPC81386
0.7674	Intermediate Similarity	NPC7563
0.7674	Intermediate Similarity	NPC320630
0.7674	Intermediate Similarity	NPC476794
0.7674	Intermediate Similarity	NPC470240
0.7674	Intermediate Similarity	NPC116177
0.767	Intermediate Similarity	NPC473975
0.767	Intermediate Similarity	NPC473843
0.767	Intermediate Similarity	NPC161816
0.767	Intermediate Similarity	NPC473594
0.767	Intermediate Similarity	NPC115257
0.767	Intermediate Similarity	NPC474586

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 NPC266957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	2289
0.2-0.3	3978
0.3-0.4	1895
0.4-0.5	559
0.5-0.6	186
0.6-0.7	28
0.7-0.8	2
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
0.8182	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1695	Approved
0.7188	Intermediate Similarity	NPD6698	Approved
0.7188	Intermediate Similarity	NPD46	Approved
0.69	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5209	Approved
0.6852	Remote Similarity	NPD6371	Approved
0.6786	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.66	Remote Similarity	NPD7983	Approved
0.6526	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5363	Approved
0.6495	Remote Similarity	NPD1694	Approved
0.6491	Remote Similarity	NPD7115	Discovery
0.6486	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5282	Discontinued
0.6458	Remote Similarity	NPD7154	Phase 3
0.6421	Remote Similarity	NPD5369	Approved
0.6354	Remote Similarity	NPD4269	Approved
0.6354	Remote Similarity	NPD4270	Approved
0.6316	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4252	Approved
0.6263	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD2067	Discontinued
0.6226	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD2204	Approved
0.617	Remote Similarity	NPD4756	Discovery
0.6168	Remote Similarity	NPD6648	Approved
0.6162	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4821	Approved
0.6146	Remote Similarity	NPD4820	Approved
0.6146	Remote Similarity	NPD4819	Approved
0.6146	Remote Similarity	NPD4822	Approved
0.6129	Remote Similarity	NPD8039	Approved
0.6126	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5362	Discontinued
0.6117	Remote Similarity	NPD5693	Phase 1
0.6111	Remote Similarity	NPD5344	Discontinued
0.6105	Remote Similarity	NPD4268	Approved
0.6105	Remote Similarity	NPD4271	Approved
0.61	Remote Similarity	NPD4249	Approved
0.6071	Remote Similarity	NPD6686	Approved
0.6058	Remote Similarity	NPD5778	Approved
0.6058	Remote Similarity	NPD5779	Approved
0.604	Remote Similarity	NPD4251	Approved
0.604	Remote Similarity	NPD4250	Approved
0.602	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD8515	Approved
0.6	Remote Similarity	NPD8517	Approved
0.6	Remote Similarity	NPD8513	Phase 3
0.598	Remote Similarity	NPD6672	Approved
0.598	Remote Similarity	NPD5737	Approved
0.5965	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5695	Phase 3
0.5926	Remote Similarity	NPD5696	Approved
0.5922	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5370	Suspended
0.5922	Remote Similarity	NPD6101	Approved
0.5902	Remote Similarity	NPD7642	Approved
0.5893	Remote Similarity	NPD6008	Approved
0.5888	Remote Similarity	NPD7839	Suspended
0.5877	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8297	Approved
0.5846	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD6084	Phase 2
0.5816	Remote Similarity	NPD5368	Approved
0.581	Remote Similarity	NPD6411	Approved
0.581	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6110	Phase 1
0.5789	Remote Similarity	NPD6881	Approved
0.5789	Remote Similarity	NPD6899	Approved
0.5785	Remote Similarity	NPD6319	Approved
0.5778	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6650	Approved
0.5776	Remote Similarity	NPD6649	Approved
0.5773	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7829	Approved
0.5772	Remote Similarity	NPD7830	Approved
0.5769	Remote Similarity	NPD6904	Approved
0.5769	Remote Similarity	NPD6080	Approved
0.5769	Remote Similarity	NPD6673	Approved
0.576	Remote Similarity	NPD8074	Phase 3
0.5755	Remote Similarity	NPD6399	Phase 3
0.5752	Remote Similarity	NPD5739	Approved
0.5752	Remote Similarity	NPD6402	Approved
0.5752	Remote Similarity	NPD6675	Approved
0.5752	Remote Similarity	NPD7128	Approved
0.5741	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6013	Approved
0.5739	Remote Similarity	NPD6372	Approved
0.5739	Remote Similarity	NPD6014	Approved
0.5739	Remote Similarity	NPD6012	Approved
0.5739	Remote Similarity	NPD6373	Approved
0.573	Remote Similarity	NPD3197	Phase 1
0.5726	Remote Similarity	NPD7492	Approved
0.5726	Remote Similarity	NPD6053	Discontinued
0.5714	Remote Similarity	NPD5692	Phase 3
0.5702	Remote Similarity	NPD5701	Approved
0.57	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6883	Approved
0.569	Remote Similarity	NPD7102	Approved
0.569	Remote Similarity	NPD7290	Approved
0.568	Remote Similarity	NPD6616	Approved
0.568	Remote Similarity	NPD8273	Phase 1
0.566	Remote Similarity	NPD5694	Approved
0.566	Remote Similarity	NPD6050	Approved
0.566	Remote Similarity	NPD7637	Suspended
0.5656	Remote Similarity	NPD6054	Approved
0.5652	Remote Similarity	NPD7320	Approved
0.5652	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6011	Approved
0.5648	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5332	Approved
0.5644	Remote Similarity	NPD5331	Approved
0.5641	Remote Similarity	NPD6869	Approved
0.5641	Remote Similarity	NPD6617	Approved
0.5641	Remote Similarity	NPD6847	Approved
0.5641	Remote Similarity	NPD8130	Phase 1
0.5641	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD7078	Approved
0.5631	Remote Similarity	NPD7334	Approved
0.5631	Remote Similarity	NPD6422	Discontinued
0.5631	Remote Similarity	NPD5330	Approved
0.5631	Remote Similarity	NPD6098	Approved
0.5631	Remote Similarity	NPD6409	Approved
0.5631	Remote Similarity	NPD7521	Approved
0.5631	Remote Similarity	NPD7146	Approved
0.5631	Remote Similarity	NPD6684	Approved
0.561	Remote Similarity	NPD6015	Approved
0.561	Remote Similarity	NPD6927	Phase 3
0.561	Remote Similarity	NPD6016	Approved
0.56	Remote Similarity	NPD4790	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data