NPASS Compound

Structure

NPC475819 OpenBabel07101718302D 31 32 0 0 1 0 0 0 0 0999 V2000 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3236 -3.1119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1646 -4.3991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9077 -5.0682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -5.6862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0667 -3.7811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.9209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9454 -5.9953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0178 -3.4720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5346 -2.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8588 -4.7592 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 0.3217 -3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 2 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 4 15 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 16 2 0 0 0 0 7 29 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 11 24 1 0 0 0 0 12 17 2 0 0 0 0 13 21 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 31 1 6 0 0 0 19 9 1 6 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 13 1 1 0 0 0 21 27 2 0 0 0 0 21 30 1 0 0 0 0 22 28 2 0 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.17
Volume:	432.612
LogP:	-0.076
LogD:	0.379
LogS:	-1.315
# Rotatable Bonds:	8
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	5.049
Fsp3:	0.545
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:	-4.877
MDCK Permeability:	6.131734699010849e-05
Pgp-inhibitor:	0.693
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.474
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	57.00267028808594%
Volume Distribution (VD):	0.297
Pgp-substrate:	57.89617919921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	3.113
Half-life (T1/2):	0.98

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.269
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.776
Skin Sensitization:	0.601
Carcinogencity:	0.189
Eye Corrosion:	0.004
Eye Irritation:	0.044
Respiratory Toxicity:	0.301

Download Data

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

Natural Product: NPC475819

Natural Product ID:	NPC475819
*Common Name:**	WWSVFCWEYPZVKN-JFQNOBTPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WWSVFCWEYPZVKN-JFQNOBTPSA-N
Standard InCHI:	InChI=1S/C22H28O9/c1-12-8-18(31-22(28)16(11-24)6-7-29-14(3)25)20-13(2)21(27)30-19(20)9-15(10-23)4-5-17(12)26/h6,9,18-20,23-24,26H,2,4-5,7-8,10-11H2,1,3H3/b15-9-,16-6+,17-12+/t18-,19+,20+/m0/s1
SMILES:	OC/C(=CCOC(=O)C)/C(=O)O[C@H]1C/C(=C(/O)CC/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/CO)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516714
PubChem CID:	n.a.
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
NPO21525	Centaurea spinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180824]
NPO21525	Centaurea spinosa	Species	Asteraceae	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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	PMID[549138]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	1.25	ug.mL-1	PMID[549138]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	5.0	ug.mL-1	PMID[549138]

☑ 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 NPC475819 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	183
0.1-0.2	1215
0.2-0.3	4909
0.3-0.4	10201
0.4-0.5	14685
0.5-0.6	7122
0.6-0.7	3308
0.7-0.8	901
0.8-0.85	76
0.85-0.9	50
0.9-0.95	32
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9634	High Similarity	NPC470755
0.9529	High Similarity	NPC474232
0.9524	High Similarity	NPC476805
0.9512	High Similarity	NPC158756
0.939	High Similarity	NPC169575
0.939	High Similarity	NPC40746
0.9286	High Similarity	NPC469910
0.9157	High Similarity	NPC116543
0.9157	High Similarity	NPC131669
0.9157	High Similarity	NPC473390
0.9146	High Similarity	NPC24417
0.9101	High Similarity	NPC471142
0.907	High Similarity	NPC476803
0.9059	High Similarity	NPC475461
0.9059	High Similarity	NPC305475
0.9048	High Similarity	NPC476804
0.9036	High Similarity	NPC229825
0.9	High Similarity	NPC230800
0.8941	High Similarity	NPC255307
0.8929	High Similarity	NPC59097
0.8902	High Similarity	NPC98557
0.8902	High Similarity	NPC167881
0.8889	High Similarity	NPC477922
0.8864	High Similarity	NPC475855
0.8824	High Similarity	NPC114979
0.8824	High Similarity	NPC96259
0.8824	High Similarity	NPC191476
0.8824	High Similarity	NPC141193
0.8791	High Similarity	NPC477921
0.878	High Similarity	NPC108816
0.878	High Similarity	NPC196653
0.878	High Similarity	NPC93763
0.878	High Similarity	NPC471465
0.8778	High Similarity	NPC474247
0.8764	High Similarity	NPC473321
0.869	High Similarity	NPC52861
0.8675	High Similarity	NPC270126
0.8667	High Similarity	NPC228451
0.8667	High Similarity	NPC125674
0.8667	High Similarity	NPC162205
0.8667	High Similarity	NPC273579
0.8667	High Similarity	NPC475838
0.8667	High Similarity	NPC288240
0.8667	High Similarity	NPC295204
0.8659	High Similarity	NPC141789
0.8659	High Similarity	NPC7563
0.8659	High Similarity	NPC476028
0.8659	High Similarity	NPC171204
0.8659	High Similarity	NPC320630
0.8659	High Similarity	NPC116177
0.8652	High Similarity	NPC179394
0.8652	High Similarity	NPC473619
0.8652	High Similarity	NPC144133
0.8636	High Similarity	NPC473715
0.8621	High Similarity	NPC150755
0.8602	High Similarity	NPC471144
0.8587	High Similarity	NPC279621
0.8571	High Similarity	NPC281132
0.8537	High Similarity	NPC68819
0.8511	High Similarity	NPC288876
0.8462	Intermediate Similarity	NPC475302
0.8444	Intermediate Similarity	NPC469368
0.8434	Intermediate Similarity	NPC97516
0.8409	Intermediate Similarity	NPC469483
0.8387	Intermediate Similarity	NPC473859
0.8333	Intermediate Similarity	NPC267231
0.8333	Intermediate Similarity	NPC474032
0.8316	Intermediate Similarity	NPC475949
0.8298	Intermediate Similarity	NPC471462
0.8295	Intermediate Similarity	NPC261380
0.8295	Intermediate Similarity	NPC21469
0.8295	Intermediate Similarity	NPC165162
0.8293	Intermediate Similarity	NPC476355
0.828	Intermediate Similarity	NPC475659
0.828	Intermediate Similarity	NPC471141
0.8261	Intermediate Similarity	NPC469645
0.8261	Intermediate Similarity	NPC469692
0.8222	Intermediate Similarity	NPC260343
0.8222	Intermediate Similarity	NPC287089
0.8214	Intermediate Similarity	NPC474760
0.8191	Intermediate Similarity	NPC306041
0.8172	Intermediate Similarity	NPC57405
0.8172	Intermediate Similarity	NPC303942
0.8172	Intermediate Similarity	NPC121825
0.8171	Intermediate Similarity	NPC295633
0.8171	Intermediate Similarity	NPC58956
0.8171	Intermediate Similarity	NPC269206
0.8161	Intermediate Similarity	NPC85772
0.8144	Intermediate Similarity	NPC149371
0.8132	Intermediate Similarity	NPC295312
0.8111	Intermediate Similarity	NPC160138
0.8111	Intermediate Similarity	NPC266957
0.8095	Intermediate Similarity	NPC123360
0.8085	Intermediate Similarity	NPC304886
0.8085	Intermediate Similarity	NPC36954
0.8072	Intermediate Similarity	NPC48641
0.8072	Intermediate Similarity	NPC476590
0.8072	Intermediate Similarity	NPC114727
0.8072	Intermediate Similarity	NPC140287
0.8068	Intermediate Similarity	NPC250315
0.8065	Intermediate Similarity	NPC475912
0.8049	Intermediate Similarity	NPC163003
0.8043	Intermediate Similarity	NPC129419
0.8043	Intermediate Similarity	NPC71533
0.8043	Intermediate Similarity	NPC106510
0.8041	Intermediate Similarity	NPC47880
0.8041	Intermediate Similarity	NPC164598
0.8041	Intermediate Similarity	NPC474339
0.8023	Intermediate Similarity	NPC19841
0.8023	Intermediate Similarity	NPC89128
0.8021	Intermediate Similarity	NPC141191
0.8	Intermediate Similarity	NPC261721
0.8	Intermediate Similarity	NPC477513
0.8	Intermediate Similarity	NPC50637
0.8	Intermediate Similarity	NPC476315
0.8	Intermediate Similarity	NPC17585
0.7979	Intermediate Similarity	NPC140543
0.7979	Intermediate Similarity	NPC474338
0.7959	Intermediate Similarity	NPC471148
0.7957	Intermediate Similarity	NPC261607
0.7957	Intermediate Similarity	NPC111114
0.7957	Intermediate Similarity	NPC300312
0.7955	Intermediate Similarity	NPC89555
0.7935	Intermediate Similarity	NPC166919
0.7935	Intermediate Similarity	NPC130359
0.7935	Intermediate Similarity	NPC218927
0.7935	Intermediate Similarity	NPC206001
0.7935	Intermediate Similarity	NPC14901
0.7935	Intermediate Similarity	NPC268298
0.7917	Intermediate Similarity	NPC169205
0.7912	Intermediate Similarity	NPC72513
0.7912	Intermediate Similarity	NPC178215
0.7895	Intermediate Similarity	NPC14961
0.7895	Intermediate Similarity	NPC270013
0.7882	Intermediate Similarity	NPC235906
0.7879	Intermediate Similarity	NPC472755
0.7872	Intermediate Similarity	NPC476300
0.7872	Intermediate Similarity	NPC165383
0.7865	Intermediate Similarity	NPC475947
0.7865	Intermediate Similarity	NPC318468
0.7857	Intermediate Similarity	NPC185141
0.7857	Intermediate Similarity	NPC46998
0.7857	Intermediate Similarity	NPC128733
0.7857	Intermediate Similarity	NPC110443
0.7857	Intermediate Similarity	NPC133907
0.7849	Intermediate Similarity	NPC473448
0.7849	Intermediate Similarity	NPC473455
0.7841	Intermediate Similarity	NPC25684
0.7841	Intermediate Similarity	NPC325031
0.7841	Intermediate Similarity	NPC301477
0.7841	Intermediate Similarity	NPC141810
0.7841	Intermediate Similarity	NPC281949
0.7835	Intermediate Similarity	NPC187268
0.7835	Intermediate Similarity	NPC473326
0.7826	Intermediate Similarity	NPC233551
0.7826	Intermediate Similarity	NPC48338
0.7826	Intermediate Similarity	NPC20339
0.7826	Intermediate Similarity	NPC40376
0.7826	Intermediate Similarity	NPC21208
0.7826	Intermediate Similarity	NPC477302
0.7826	Intermediate Similarity	NPC280621
0.7826	Intermediate Similarity	NPC136879
0.7826	Intermediate Similarity	NPC202672
0.7816	Intermediate Similarity	NPC470244
0.7816	Intermediate Similarity	NPC470239
0.7816	Intermediate Similarity	NPC178277
0.7812	Intermediate Similarity	NPC185553
0.7802	Intermediate Similarity	NPC134865
0.7802	Intermediate Similarity	NPC103523
0.78	Intermediate Similarity	NPC100487
0.78	Intermediate Similarity	NPC475676
0.78	Intermediate Similarity	NPC220964
0.7789	Intermediate Similarity	NPC469632
0.7789	Intermediate Similarity	NPC476267
0.7789	Intermediate Similarity	NPC81386
0.7789	Intermediate Similarity	NPC477131
0.7789	Intermediate Similarity	NPC167219
0.7789	Intermediate Similarity	NPC474035
0.7789	Intermediate Similarity	NPC471147
0.7778	Intermediate Similarity	NPC197835
0.7778	Intermediate Similarity	NPC140591
0.7778	Intermediate Similarity	NPC303653
0.7778	Intermediate Similarity	NPC189609
0.7778	Intermediate Similarity	NPC291500
0.7766	Intermediate Similarity	NPC30515
0.7766	Intermediate Similarity	NPC184463
0.7766	Intermediate Similarity	NPC158061
0.7766	Intermediate Similarity	NPC475925
0.7765	Intermediate Similarity	NPC155587
0.7755	Intermediate Similarity	NPC477512
0.7753	Intermediate Similarity	NPC475046
0.7753	Intermediate Similarity	NPC310450
0.7753	Intermediate Similarity	NPC11383
0.7753	Intermediate Similarity	NPC474959
0.7753	Intermediate Similarity	NPC474252
0.7742	Intermediate Similarity	NPC87306
0.7742	Intermediate Similarity	NPC139418
0.7732	Intermediate Similarity	NPC40812
0.7732	Intermediate Similarity	NPC471140
0.7711	Intermediate Similarity	NPC67183

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 NPC475819 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1796
0.2-0.3	3703
0.3-0.4	2362
0.4-0.5	752
0.5-0.6	305
0.6-0.7	45
0.7-0.8	21
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
0.7708	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5785	Approved
0.766	Intermediate Similarity	NPD46	Approved
0.766	Intermediate Similarity	NPD6698	Approved
0.75	Intermediate Similarity	NPD5363	Approved
0.7476	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7154	Phase 3
0.7396	Intermediate Similarity	NPD7983	Approved
0.7312	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4225	Approved
0.7264	Intermediate Similarity	NPD6371	Approved
0.7234	Intermediate Similarity	NPD4249	Approved
0.7174	Intermediate Similarity	NPD4270	Approved
0.7174	Intermediate Similarity	NPD4269	Approved
0.7158	Intermediate Similarity	NPD4250	Approved
0.7158	Intermediate Similarity	NPD4251	Approved
0.7143	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4252	Approved
0.7113	Intermediate Similarity	NPD7838	Discovery
0.7053	Intermediate Similarity	NPD5786	Approved
0.697	Remote Similarity	NPD5778	Approved
0.697	Remote Similarity	NPD5779	Approved
0.6961	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7839	Suspended
0.6923	Remote Similarity	NPD4268	Approved
0.6923	Remote Similarity	NPD4271	Approved
0.6915	Remote Similarity	NPD5362	Discontinued
0.69	Remote Similarity	NPD5282	Discontinued
0.6882	Remote Similarity	NPD5369	Approved
0.6837	Remote Similarity	NPD1695	Approved
0.6809	Remote Similarity	NPD5209	Approved
0.6774	Remote Similarity	NPD4819	Approved
0.6774	Remote Similarity	NPD4821	Approved
0.6774	Remote Similarity	NPD4820	Approved
0.6774	Remote Similarity	NPD4822	Approved
0.6771	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6686	Approved
0.6727	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5370	Suspended
0.6632	Remote Similarity	NPD6435	Approved
0.6632	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4756	Discovery
0.6598	Remote Similarity	NPD1694	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7637	Suspended
0.6535	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6053	Discontinued
0.65	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8517	Approved
0.6496	Remote Similarity	NPD8513	Phase 3
0.6496	Remote Similarity	NPD8516	Approved
0.6496	Remote Similarity	NPD8515	Approved
0.6495	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5368	Approved
0.6415	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD7640	Approved
0.6392	Remote Similarity	NPD5332	Approved
0.6392	Remote Similarity	NPD5331	Approved
0.6373	Remote Similarity	NPD6411	Approved
0.6355	Remote Similarity	NPD5344	Discontinued
0.6354	Remote Similarity	NPD4790	Discontinued
0.6322	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7638	Approved
0.623	Remote Similarity	NPD8074	Phase 3
0.6224	Remote Similarity	NPD6110	Phase 1
0.618	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6399	Phase 3
0.6116	Remote Similarity	NPD7830	Approved
0.6116	Remote Similarity	NPD7829	Approved
0.6116	Remote Similarity	NPD7642	Approved
0.6111	Remote Similarity	NPD6648	Approved
0.6064	Remote Similarity	NPD8039	Approved
0.6053	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD2204	Approved
0.6	Remote Similarity	NPD6649	Approved
0.5965	Remote Similarity	NPD6373	Approved
0.5965	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6372	Approved
0.5946	Remote Similarity	NPD6647	Phase 2
0.5929	Remote Similarity	NPD5697	Approved
0.5926	Remote Similarity	NPD6084	Phase 2
0.5926	Remote Similarity	NPD7902	Approved
0.5926	Remote Similarity	NPD6083	Phase 2
0.5923	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6421	Discontinued
0.5909	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3704	Approved
0.5888	Remote Similarity	NPD5695	Phase 3
0.5887	Remote Similarity	NPD8273	Phase 1
0.5882	Remote Similarity	NPD6422	Discontinued
0.5877	Remote Similarity	NPD6899	Approved
0.5877	Remote Similarity	NPD6881	Approved
0.5873	Remote Similarity	NPD7319	Approved
0.5872	Remote Similarity	NPD5696	Approved
0.5868	Remote Similarity	NPD6319	Approved
0.5862	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7632	Discontinued
0.5843	Remote Similarity	NPD3197	Phase 1
0.5841	Remote Similarity	NPD6402	Approved
0.5841	Remote Similarity	NPD7128	Approved
0.5841	Remote Similarity	NPD6675	Approved
0.5841	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD7641	Discontinued
0.5833	Remote Similarity	NPD4228	Discovery
0.5826	Remote Similarity	NPD6013	Approved
0.5826	Remote Similarity	NPD6012	Approved
0.5826	Remote Similarity	NPD6014	Approved
0.582	Remote Similarity	NPD8444	Approved
0.5812	Remote Similarity	NPD6882	Approved
0.5812	Remote Similarity	NPD8297	Approved
0.58	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7748	Approved
0.5789	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD7260	Phase 2
0.5776	Remote Similarity	NPD7102	Approved
0.5776	Remote Similarity	NPD7290	Approved
0.5776	Remote Similarity	NPD6883	Approved
0.5776	Remote Similarity	NPD2067	Discontinued
0.576	Remote Similarity	NPD7507	Approved
0.576	Remote Similarity	NPD8451	Approved
0.5758	Remote Similarity	NPD4695	Discontinued
0.5755	Remote Similarity	NPD7515	Phase 2
0.5739	Remote Similarity	NPD6011	Approved
0.5739	Remote Similarity	NPD7320	Approved
0.5728	Remote Similarity	NPD7334	Approved
0.5728	Remote Similarity	NPD6684	Approved
0.5728	Remote Similarity	NPD5330	Approved
0.5728	Remote Similarity	NPD6409	Approved
0.5728	Remote Similarity	NPD7146	Approved
0.5728	Remote Similarity	NPD3618	Phase 1
0.5728	Remote Similarity	NPD7521	Approved
0.5726	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD8130	Phase 1
0.5726	Remote Similarity	NPD6869	Approved
0.5726	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD3732	Approved
0.5714	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5703	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6008	Approved
0.5688	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD3133	Approved
0.5686	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD3666	Approved
0.5686	Remote Similarity	NPD3665	Phase 1
0.568	Remote Similarity	NPD8342	Approved
0.568	Remote Similarity	NPD8341	Approved
0.568	Remote Similarity	NPD8340	Approved
0.568	Remote Similarity	NPD8299	Approved
0.568	Remote Similarity	NPD7492	Approved
0.5652	Remote Similarity	NPD6412	Phase 2
0.5648	Remote Similarity	NPD7900	Approved
0.5648	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD3667	Approved
0.5635	Remote Similarity	NPD6616	Approved
0.562	Remote Similarity	NPD7505	Discontinued
0.5619	Remote Similarity	NPD6903	Approved
0.5619	Remote Similarity	NPD6672	Approved
0.5619	Remote Similarity	NPD5737	Approved
0.5619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD368	Approved
0.5615	Remote Similarity	NPD6845	Suspended
0.5614	Remote Similarity	NPD5141	Approved
0.561	Remote Similarity	NPD6054	Approved
0.5607	Remote Similarity	NPD5281	Approved
0.5607	Remote Similarity	NPD5284	Approved
0.5607	Remote Similarity	NPD5693	Phase 1
0.5603	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8328	Phase 3

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