NPASS Compound

Structure

CID218510 OpenBabel06191716012D 33 36 0 0 1 0 0 0 0 0999 V2000 -4.5217 -2.7853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7043 -1.6027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3311 -0.1444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1592 3.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7907 2.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 2.5494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3697 2.0180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2118 -1.9100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7214 -1.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6328 1.1976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5568 -0.7664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1592 -1.9100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8290 -1.2401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4559 -0.5069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5419 -1.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1592 0.3771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1592 2.0180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 -1.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5419 -0.2928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2118 0.3771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8290 -0.2928 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2118 2.0180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 -0.2928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7214 0.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7381 1.1976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3322 -1.4462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6328 2.8385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7381 2.8385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7214 2.0757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8434 1.1976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5329 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 -5.7043 0.0698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 14 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 31 1 0 0 0 0 11 32 1 0 0 0 0 12 1 1 6 0 0 0 12 13 1 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 14 26 2 0 0 0 0 14 33 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 27 1 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 24 2 0 0 0 0 20 25 2 0 0 0 0 21 33 1 1 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 32 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.19
Volume:	458.597
LogP:	3.747
LogD:	3.453
LogS:	-5.005
# Rotatable Bonds:	6
TPSA:	81.68
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	3.85
Fsp3:	0.48
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.733
MDCK Permeability:	2.9105876819812693e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	80.20099639892578%
Volume Distribution (VD):	0.85
Pgp-substrate:	11.51899528503418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.61
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.787
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.894

ADMET: Excretion

Clearance (CL):	4.212
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.299
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.113
Carcinogencity:	0.481
Eye Corrosion:	0.003
Eye Irritation:	0.077
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC218510

Natural Product ID:	NPC218510
*Common Name:**	Rubschisantherin
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GRHNKVUUWRVFMM-OYMPBJRDSA-N
Standard InCHI:	InChI=1S/C25H30O8/c1-12-8-15-9-18-23(32-11-31-18)24(29-6)19(15)20-16(21(13(12)2)33-14(3)26)10-17(27-4)22(28-5)25(20)30-7/h9-10,12-13,21H,8,11H2,1-7H3/t12-,13-,21+/m0/s1
SMILES:	C[C@H]1Cc2cc3c(c(c2-c2c(cc(c(c2OC)OC)OC)[C@@H]([C@H]1C)OC(=O)C)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386335
PubChem CID:	73353444
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	Stems	Luoji Mountain Village, Xichang County, Sicuan Province, China	2011-Sep	PMID[23738539]
NPO29191	Schisandra neglecta	Species	Schisandraceae	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
EC50	1
IC50	5
Others	2

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	85200.0	nM	PMID[533201]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[533201]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[533201]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[533201]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[533201]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	4700.0	nM	PMID[533201]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	18.2	n.a.	PMID[533201]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[533201]

☑ 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 NPC218510 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	391
0.1-0.2	1568
0.2-0.3	4004
0.3-0.4	10259
0.4-0.5	8465
0.5-0.6	4508
0.6-0.7	8891
0.7-0.8	3898
0.8-0.85	461
0.85-0.9	175
0.9-0.95	59
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76415
0.9926	High Similarity	NPC326144
0.9854	High Similarity	NPC327651
0.9854	High Similarity	NPC318286
0.9783	High Similarity	NPC321696
0.9783	High Similarity	NPC321958
0.9643	High Similarity	NPC477375
0.9643	High Similarity	NPC198129
0.9643	High Similarity	NPC327352
0.9643	High Similarity	NPC325720
0.9643	High Similarity	NPC316676
0.9643	High Similarity	NPC252281
0.9574	High Similarity	NPC85141
0.9574	High Similarity	NPC322426
0.9574	High Similarity	NPC477374
0.9574	High Similarity	NPC477376
0.9507	High Similarity	NPC316989
0.9507	High Similarity	NPC473989
0.9485	High Similarity	NPC865
0.9441	High Similarity	NPC303519
0.9441	High Similarity	NPC475756
0.9441	High Similarity	NPC224472
0.9407	High Similarity	NPC145722
0.9407	High Similarity	NPC256776
0.9407	High Similarity	NPC185680
0.9375	High Similarity	NPC471154
0.9375	High Similarity	NPC475229
0.9375	High Similarity	NPC477378
0.931	High Similarity	NPC24562
0.931	High Similarity	NPC53669
0.931	High Similarity	NPC217708
0.931	High Similarity	NPC308739
0.931	High Similarity	NPC477377
0.931	High Similarity	NPC126405
0.931	High Similarity	NPC297271
0.931	High Similarity	NPC77237
0.931	High Similarity	NPC474606
0.931	High Similarity	NPC16791
0.9286	High Similarity	NPC324962
0.927	High Similarity	NPC11453
0.927	High Similarity	NPC32189
0.927	High Similarity	NPC143895
0.9247	High Similarity	NPC178195
0.9247	High Similarity	NPC348849
0.9247	High Similarity	NPC312763
0.9247	High Similarity	NPC198461
0.9247	High Similarity	NPC473425
0.9214	High Similarity	NPC229172
0.9214	High Similarity	NPC36531
0.9214	High Similarity	NPC230538
0.9214	High Similarity	NPC103637
0.9209	High Similarity	NPC216434
0.9209	High Similarity	NPC103448
0.9184	High Similarity	NPC238834
0.9184	High Similarity	NPC476065
0.9178	High Similarity	NPC474514
0.9155	High Similarity	NPC475868
0.9137	High Similarity	NPC201404
0.9137	High Similarity	NPC53722
0.9137	High Similarity	NPC290714
0.9122	High Similarity	NPC477380
0.9122	High Similarity	NPC473323
0.9122	High Similarity	NPC29727
0.9085	High Similarity	NPC73467
0.9085	High Similarity	NPC87883
0.9085	High Similarity	NPC172171
0.9085	High Similarity	NPC239254
0.9085	High Similarity	NPC121661
0.9078	High Similarity	NPC287124
0.9078	High Similarity	NPC474295
0.906	High Similarity	NPC477885
0.906	High Similarity	NPC475592
0.9044	High Similarity	NPC141493
0.9044	High Similarity	NPC184928
0.9021	High Similarity	NPC197352
0.9021	High Similarity	NPC166506
0.9021	High Similarity	NPC189239
0.9021	High Similarity	NPC110763
0.9	High Similarity	NPC215400
0.9	High Similarity	NPC325122
0.9	High Similarity	NPC230531
0.8978	High Similarity	NPC475856
0.8978	High Similarity	NPC261812
0.8978	High Similarity	NPC65183
0.8978	High Similarity	NPC72046
0.8973	High Similarity	NPC24425
0.8958	High Similarity	NPC154971
0.8958	High Similarity	NPC252286
0.8958	High Similarity	NPC474054
0.8951	High Similarity	NPC477701
0.8951	High Similarity	NPC141569
0.8951	High Similarity	NPC18211
0.8951	High Similarity	NPC474036
0.8951	High Similarity	NPC166884
0.8951	High Similarity	NPC143092
0.8944	High Similarity	NPC133934
0.8944	High Similarity	NPC184684
0.8944	High Similarity	NPC184641
0.894	High Similarity	NPC63061
0.8929	High Similarity	NPC196420
0.8921	High Similarity	NPC49235
0.8921	High Similarity	NPC25333
0.8921	High Similarity	NPC148893
0.8913	High Similarity	NPC136750
0.8913	High Similarity	NPC1474
0.8913	High Similarity	NPC266848
0.8912	High Similarity	NPC210642
0.8912	High Similarity	NPC13985
0.8897	High Similarity	NPC295297
0.8889	High Similarity	NPC477702
0.8882	High Similarity	NPC191352
0.8882	High Similarity	NPC319749
0.8882	High Similarity	NPC258322
0.8873	High Similarity	NPC312199
0.8859	High Similarity	NPC273578
0.8857	High Similarity	NPC121651
0.8849	High Similarity	NPC31530
0.8844	High Similarity	NPC149505
0.8841	High Similarity	NPC7744
0.8836	High Similarity	NPC304821
0.8836	High Similarity	NPC477879
0.8828	High Similarity	NPC212890
0.8824	High Similarity	NPC280778
0.8824	High Similarity	NPC283114
0.8824	High Similarity	NPC207702
0.8824	High Similarity	NPC149008
0.8811	High Similarity	NPC40237
0.8811	High Similarity	NPC151423
0.88	High Similarity	NPC117154
0.8786	High Similarity	NPC474139
0.8786	High Similarity	NPC189474
0.8776	High Similarity	NPC474393
0.8776	High Similarity	NPC474347
0.8768	High Similarity	NPC192255
0.8732	High Similarity	NPC113550
0.8725	High Similarity	NPC302610
0.8716	High Similarity	NPC470916
0.8716	High Similarity	NPC477381
0.871	High Similarity	NPC477884
0.8699	High Similarity	NPC87295
0.8696	High Similarity	NPC237169
0.8696	High Similarity	NPC476399
0.8696	High Similarity	NPC470624
0.869	High Similarity	NPC92693
0.869	High Similarity	NPC475000
0.869	High Similarity	NPC218841
0.8686	High Similarity	NPC281864
0.8686	High Similarity	NPC328682
0.8686	High Similarity	NPC54321
0.8684	High Similarity	NPC207584
0.8684	High Similarity	NPC19947
0.8681	High Similarity	NPC176586
0.8681	High Similarity	NPC472562
0.8681	High Similarity	NPC210354
0.8681	High Similarity	NPC80326
0.8676	High Similarity	NPC50683
0.8676	High Similarity	NPC9891
0.8676	High Similarity	NPC112571
0.8676	High Similarity	NPC88297
0.8676	High Similarity	NPC186845
0.8676	High Similarity	NPC285725
0.8671	High Similarity	NPC46591
0.8667	High Similarity	NPC245948
0.8662	High Similarity	NPC261714
0.8662	High Similarity	NPC283949
0.8658	High Similarity	NPC477379
0.8654	High Similarity	NPC83049
0.8654	High Similarity	NPC118162
0.8654	High Similarity	NPC320471
0.8652	High Similarity	NPC72796
0.8652	High Similarity	NPC236522
0.8652	High Similarity	NPC150534
0.8652	High Similarity	NPC44245
0.8652	High Similarity	NPC224941
0.8652	High Similarity	NPC311430
0.8643	High Similarity	NPC196937
0.8639	High Similarity	NPC304687
0.8639	High Similarity	NPC101755
0.8639	High Similarity	NPC137352
0.8639	High Similarity	NPC80230
0.8639	High Similarity	NPC104024
0.8639	High Similarity	NPC65574
0.8639	High Similarity	NPC183083
0.8623	High Similarity	NPC476748
0.8621	High Similarity	NPC474288
0.8618	High Similarity	NPC237946
0.8618	High Similarity	NPC32373
0.8613	High Similarity	NPC473093
0.8613	High Similarity	NPC8050
0.8613	High Similarity	NPC473092
0.8611	High Similarity	NPC300798
0.8611	High Similarity	NPC58137
0.8601	High Similarity	NPC471183
0.86	High Similarity	NPC220577
0.8599	High Similarity	NPC79322
0.8599	High Similarity	NPC311912
0.8592	High Similarity	NPC197166
0.8592	High Similarity	NPC133025
0.8581	High Similarity	NPC40654
0.8581	High Similarity	NPC262804

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 NPC218510 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	934
0.2-0.3	1912
0.3-0.4	2780
0.4-0.5	1643
0.5-0.6	944
0.6-0.7	526
0.7-0.8	87
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD37	Approved
0.8618	High Similarity	NPD4967	Phase 2
0.8618	High Similarity	NPD4965	Approved
0.8618	High Similarity	NPD4966	Approved
0.8506	High Similarity	NPD6234	Discontinued
0.8444	Intermediate Similarity	NPD3705	Approved
0.828	Intermediate Similarity	NPD7199	Phase 2
0.8176	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7228	Approved
0.7974	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7240	Approved
0.7847	Intermediate Similarity	NPD3027	Phase 3
0.7792	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3018	Phase 2
0.7692	Intermediate Similarity	NPD1653	Approved
0.7647	Intermediate Similarity	NPD5283	Phase 1
0.7632	Intermediate Similarity	NPD6674	Discontinued
0.7606	Intermediate Similarity	NPD2981	Phase 2
0.7568	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1613	Approved
0.7552	Intermediate Similarity	NPD2983	Phase 2
0.7552	Intermediate Similarity	NPD2982	Phase 2
0.7548	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7466	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6232	Discontinued
0.745	Intermediate Similarity	NPD4060	Phase 1
0.744	Intermediate Similarity	NPD5844	Phase 1
0.7439	Intermediate Similarity	NPD5494	Approved
0.7434	Intermediate Similarity	NPD2438	Suspended
0.7425	Intermediate Similarity	NPD7473	Discontinued
0.7415	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3817	Phase 2
0.7386	Intermediate Similarity	NPD7266	Discontinued
0.7384	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5691	Approved
0.7317	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4908	Phase 1
0.7294	Intermediate Similarity	NPD7074	Phase 3
0.7278	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5763	Approved
0.7273	Intermediate Similarity	NPD5762	Approved
0.7246	Intermediate Similarity	NPD7229	Phase 3
0.7241	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1465	Phase 2
0.7235	Intermediate Similarity	NPD7054	Approved
0.7233	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2979	Phase 3
0.7209	Intermediate Similarity	NPD6559	Discontinued
0.7208	Intermediate Similarity	NPD3539	Phase 1
0.7203	Intermediate Similarity	NPD1357	Approved
0.72	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7472	Approved
0.7178	Intermediate Similarity	NPD1934	Approved
0.7172	Intermediate Similarity	NPD1610	Phase 2
0.7172	Intermediate Similarity	NPD1611	Approved
0.7171	Intermediate Similarity	NPD6355	Discontinued
0.7169	Intermediate Similarity	NPD919	Approved
0.7168	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3540	Phase 1
0.7143	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7134	Intermediate Similarity	NPD7819	Suspended
0.7134	Intermediate Similarity	NPD4110	Phase 3
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.712	Intermediate Similarity	NPD7680	Approved
0.7115	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2861	Phase 2
0.7101	Intermediate Similarity	NPD3926	Phase 2
0.7091	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7808	Phase 3
0.7065	Intermediate Similarity	NPD5005	Approved
0.7065	Intermediate Similarity	NPD5006	Approved
0.7063	Intermediate Similarity	NPD2532	Approved
0.7063	Intermediate Similarity	NPD5536	Phase 2
0.7063	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD2534	Approved
0.7062	Intermediate Similarity	NPD6842	Approved
0.7062	Intermediate Similarity	NPD6841	Approved
0.7062	Intermediate Similarity	NPD6843	Phase 3
0.7059	Intermediate Similarity	NPD3657	Discovery
0.7059	Intermediate Similarity	NPD4481	Phase 3
0.7055	Intermediate Similarity	NPD1091	Approved
0.7055	Intermediate Similarity	NPD1281	Approved
0.7052	Intermediate Similarity	NPD6797	Phase 2
0.7048	Intermediate Similarity	NPD3882	Suspended
0.7047	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7124	Phase 2
0.7041	Intermediate Similarity	NPD3787	Discontinued
0.7034	Intermediate Similarity	NPD4626	Approved
0.7032	Intermediate Similarity	NPD4108	Discontinued
0.703	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7251	Discontinued
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4055	Discovery
0.7	Intermediate Similarity	NPD5242	Approved
0.6994	Remote Similarity	NPD4005	Discontinued
0.6993	Remote Similarity	NPD3620	Phase 2
0.6993	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4140	Approved
0.6988	Remote Similarity	NPD5353	Approved
0.6982	Remote Similarity	NPD8127	Discontinued
0.6974	Remote Similarity	NPD5110	Phase 2
0.6974	Remote Similarity	NPD5111	Phase 2
0.6974	Remote Similarity	NPD5109	Approved
0.6971	Remote Similarity	NPD7549	Discontinued
0.697	Remote Similarity	NPD3382	Approved
0.697	Remote Similarity	NPD3384	Approved
0.697	Remote Similarity	NPD3383	Approved
0.6968	Remote Similarity	NPD6111	Discontinued
0.6968	Remote Similarity	NPD7097	Phase 1
0.6966	Remote Similarity	NPD5585	Approved
0.6962	Remote Similarity	NPD1652	Phase 2
0.6962	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4749	Approved
0.6959	Remote Similarity	NPD6166	Phase 2
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5535	Approved
0.6948	Remote Similarity	NPD5124	Phase 1
0.6948	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1933	Approved
0.6943	Remote Similarity	NPD1375	Discontinued
0.694	Remote Similarity	NPD4420	Approved
0.6939	Remote Similarity	NPD422	Phase 1
0.6928	Remote Similarity	NPD2801	Approved
0.6927	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3892	Phase 2
0.6918	Remote Similarity	NPD3750	Approved
0.6918	Remote Similarity	NPD17	Approved
0.6914	Remote Similarity	NPD7685	Pre-registration
0.6913	Remote Similarity	NPD1283	Approved
0.6909	Remote Similarity	NPD5089	Approved
0.6909	Remote Similarity	NPD5090	Approved
0.6897	Remote Similarity	NPD1548	Phase 1
0.6894	Remote Similarity	NPD6799	Approved
0.6882	Remote Similarity	NPD1247	Approved
0.6879	Remote Similarity	NPD2531	Phase 2
0.6879	Remote Similarity	NPD2796	Approved
0.6863	Remote Similarity	NPD6798	Discontinued
0.6863	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1651	Approved
0.6848	Remote Similarity	NPD7028	Phase 2
0.6848	Remote Similarity	NPD6599	Discontinued
0.6846	Remote Similarity	NPD5327	Phase 3
0.6846	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1358	Approved
0.6832	Remote Similarity	NPD5058	Phase 3
0.6832	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4210	Discontinued
0.6826	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4585	Approved
0.6815	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7466	Approved
0.6813	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD709	Approved
0.6805	Remote Similarity	NPD7075	Discontinued
0.6803	Remote Similarity	NPD5125	Phase 3
0.6803	Remote Similarity	NPD5126	Approved
0.6797	Remote Similarity	NPD7095	Approved
0.679	Remote Similarity	NPD4357	Discontinued
0.6786	Remote Similarity	NPD5402	Approved
0.6784	Remote Similarity	NPD6959	Discontinued
0.6782	Remote Similarity	NPD3751	Discontinued
0.6779	Remote Similarity	NPD1608	Approved
0.6772	Remote Similarity	NPD6100	Approved
0.6772	Remote Similarity	NPD6099	Approved
0.6772	Remote Similarity	NPD6032	Approved
0.6768	Remote Similarity	NPD920	Approved
0.6766	Remote Similarity	NPD6801	Discontinued
0.6763	Remote Similarity	NPD3134	Approved
0.6758	Remote Similarity	NPD7296	Approved
0.6757	Remote Similarity	NPD3496	Discontinued
0.6753	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4237	Approved
0.675	Remote Similarity	NPD4236	Phase 3
0.675	Remote Similarity	NPD1243	Approved
0.6748	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4380	Phase 2
0.6743	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4359	Approved
0.6732	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD230	Phase 1
0.673	Remote Similarity	NPD6002	Phase 3
0.673	Remote Similarity	NPD6005	Phase 3
0.673	Remote Similarity	NPD6006	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