NPASS Compound

Structure

NPC280778 OpenBabel07101719252D 39 44 0 0 1 0 0 0 0 0999 V2000 0.8926 -0.8012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2587 5.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6500 4.8769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5483 4.5849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0847 4.0485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7114 2.5973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9525 3.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5866 1.6489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0688 2.8135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7028 1.2829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2152 0.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7199 0.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7804 3.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 0.8837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0202 1.2371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2587 0.0825 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9440 1.8652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8915 0.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2587 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2587 4.0485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5483 0.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8915 1.7154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2152 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2152 4.0485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5483 1.7154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7199 2.1936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6934 3.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5823 1.7154 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0603 1.4991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5823 0.7589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9354 0.5508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7804 4.8769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6934 4.8769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7199 4.1067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6065 3.2201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4580 0.4633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4580 2.0110 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 -0.3014 2.0814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 16 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 19 2 0 0 0 0 13 20 1 0 0 0 0 14 38 1 0 0 0 0 15 36 1 0 0 0 0 15 37 1 0 0 0 0 16 30 1 6 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 28 1 0 0 0 0 20 24 2 0 0 0 0 20 32 1 0 0 0 0 21 25 2 0 0 0 0 21 36 1 0 0 0 0 22 23 1 0 0 0 0 22 26 2 0 0 0 0 23 27 2 0 0 0 0 24 27 1 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 37 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 30 1 1 0 0 0 28 39 1 0 0 0 0 29 31 2 0 0 0 0 29 39 1 0 0 0 0 30 14 1 6 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.19
Volume:	528.845
LogP:	4.811
LogD:	3.648
LogS:	-6.057
# Rotatable Bonds:	7
TPSA:	94.21
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	4.392
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.796
MDCK Permeability:	4.639248436433263e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	85.11173248291016%
Volume Distribution (VD):	0.47
Pgp-substrate:	8.161768913269043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.738
CYP2C9-inhibitor:	0.909
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.772

ADMET: Excretion

Clearance (CL):	10.892
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.2
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.376
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.531
Skin Sensitization:	0.214
Carcinogencity:	0.813
Eye Corrosion:	0.003
Eye Irritation:	0.167
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC280778

Natural Product ID:	NPC280778
*Common Name:**	Schisandrin A1
IUPAC Name:	n.a.
Synonyms:	schisandrin A1
Standard InCHIKey:	DTXYSUBZXXXZKK-VLPWJMHXSA-N
Standard InCHI:	InChI=1S/C30H30O9/c1-16-11-18-12-21-25(37-15-36-21)26(34-4)22(18)23-19(13-20(32-2)24(33-3)27(23)35-5)28(30(16)14-38-30)39-29(31)17-9-7-6-8-10-17/h6-10,12-13,16,28H,11,14-15H2,1-5H3/t16-,28-,30+/m0/s1
SMILES:	COc1cc2c(c(c1OC)OC)c1c(cc3c(c1OC)OCO3)C[C@@H]([C@@]1([C@H]2OC(=O)c2ccccc2)CO1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2313859
PubChem CID:	71530366
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
NPO33401	schisandra sphenathera	Species	Schisandraceae	Eukaryota	stems	n.a.	n.a.	PMID[23237974]

☑ 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	4
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	100000.0	nM	PMID[544346]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	50800.0	nM	PMID[544346]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	97.5	ug.mL-1	PMID[544346]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[544346]

☑ 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 NPC280778 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	449
0.1-0.2	1616
0.2-0.3	3598
0.3-0.4	9088
0.4-0.5	9649
0.5-0.6	3807
0.6-0.7	6909
0.7-0.8	7220
0.8-0.85	281
0.85-0.9	58
0.9-0.95	18
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC191352
0.9677	High Similarity	NPC319749
0.9677	High Similarity	NPC258322
0.9557	High Similarity	NPC320471
0.9557	High Similarity	NPC83049
0.9557	High Similarity	NPC118162
0.9497	High Similarity	NPC79322
0.9494	High Similarity	NPC477884
0.9437	High Similarity	NPC88557
0.9375	High Similarity	NPC311912
0.9299	High Similarity	NPC325122
0.9264	High Similarity	NPC477881
0.9226	High Similarity	NPC477377
0.9172	High Similarity	NPC477380
0.9167	High Similarity	NPC348849
0.9167	High Similarity	NPC178195
0.9161	High Similarity	NPC475229
0.9161	High Similarity	NPC477378
0.9141	High Similarity	NPC477883
0.9114	High Similarity	NPC477885
0.9096	High Similarity	NPC477880
0.9096	High Similarity	NPC477882
0.9032	High Similarity	NPC316989
0.9026	High Similarity	NPC252281
0.9026	High Similarity	NPC327352
0.9026	High Similarity	NPC198129
0.9026	High Similarity	NPC477375
0.9006	High Similarity	NPC42797
0.8974	High Similarity	NPC303519
0.8968	High Similarity	NPC85141
0.8968	High Similarity	NPC477374
0.8968	High Similarity	NPC322426
0.8968	High Similarity	NPC477376
0.8951	High Similarity	NPC291977
0.8938	High Similarity	NPC474043
0.8938	High Similarity	NPC328122
0.8938	High Similarity	NPC125713
0.8917	High Similarity	NPC220577
0.8896	High Similarity	NPC321958
0.8896	High Similarity	NPC321696
0.8889	High Similarity	NPC473445
0.8889	High Similarity	NPC249070
0.8889	High Similarity	NPC61141
0.8861	High Similarity	NPC126405
0.8861	High Similarity	NPC16791
0.8861	High Similarity	NPC77237
0.8861	High Similarity	NPC297271
0.8861	High Similarity	NPC217708
0.8861	High Similarity	NPC308739
0.8861	High Similarity	NPC53669
0.8855	High Similarity	NPC469506
0.8831	High Similarity	NPC327651
0.8831	High Similarity	NPC318286
0.8824	High Similarity	NPC76415
0.8824	High Similarity	NPC218510
0.882	High Similarity	NPC215400
0.882	High Similarity	NPC230531
0.8812	High Similarity	NPC301897
0.8812	High Similarity	NPC115123
0.8812	High Similarity	NPC239113
0.8805	High Similarity	NPC198461
0.8797	High Similarity	NPC104353
0.8766	High Similarity	NPC326144
0.875	High Similarity	NPC234730
0.8742	High Similarity	NPC474514
0.8742	High Similarity	NPC24562
0.8734	High Similarity	NPC13985
0.8734	High Similarity	NPC224472
0.8734	High Similarity	NPC210642
0.8727	High Similarity	NPC474042
0.8727	High Similarity	NPC174734
0.872	High Similarity	NPC475865
0.8688	High Similarity	NPC312763
0.8688	High Similarity	NPC273578
0.8675	High Similarity	NPC471180
0.8671	High Similarity	NPC149505
0.865	High Similarity	NPC474770
0.865	High Similarity	NPC78944
0.8645	High Similarity	NPC474036
0.8642	High Similarity	NPC475592
0.8642	High Similarity	NPC19600
0.8634	High Similarity	NPC238834
0.8634	High Similarity	NPC476065
0.8623	High Similarity	NPC117911
0.8614	High Similarity	NPC471923
0.8598	High Similarity	NPC209411
0.8598	High Similarity	NPC239890
0.858	High Similarity	NPC474568
0.858	High Similarity	NPC473900
0.858	High Similarity	NPC473323
0.8563	High Similarity	NPC473531
0.8563	High Similarity	NPC475453
0.8562	High Similarity	NPC118332
0.8545	High Similarity	NPC116838
0.8545	High Similarity	NPC22130
0.8544	High Similarity	NPC262804
0.8544	High Similarity	NPC40654
0.8544	High Similarity	NPC325720
0.8544	High Similarity	NPC316676
0.8537	High Similarity	NPC96593
0.8528	High Similarity	NPC19947
0.8528	High Similarity	NPC207584
0.8526	High Similarity	NPC18211
0.8526	High Similarity	NPC143092
0.8526	High Similarity	NPC475000
0.8521	High Similarity	NPC178737
0.8521	High Similarity	NPC471181
0.8509	High Similarity	NPC474606
0.8509	High Similarity	NPC245948
0.85	High Similarity	NPC475756
0.8494	Intermediate Similarity	NPC469518
0.8494	Intermediate Similarity	NPC469475
0.8485	Intermediate Similarity	NPC15212
0.8485	Intermediate Similarity	NPC288149
0.8481	Intermediate Similarity	NPC295297
0.8481	Intermediate Similarity	NPC101755
0.8481	Intermediate Similarity	NPC65574
0.8481	Intermediate Similarity	NPC80230
0.8481	Intermediate Similarity	NPC104024
0.8481	Intermediate Similarity	NPC304687
0.848	Intermediate Similarity	NPC196771
0.8471	Intermediate Similarity	NPC474158
0.8471	Intermediate Similarity	NPC184624
0.8466	Intermediate Similarity	NPC29727
0.8466	Intermediate Similarity	NPC237946
0.8466	Intermediate Similarity	NPC32373
0.8457	Intermediate Similarity	NPC473736
0.8457	Intermediate Similarity	NPC54179
0.8457	Intermediate Similarity	NPC473425
0.8447	Intermediate Similarity	NPC476434
0.8447	Intermediate Similarity	NPC471154
0.8438	Intermediate Similarity	NPC473989
0.8434	Intermediate Similarity	NPC469512
0.8428	Intermediate Similarity	NPC304821
0.8418	Intermediate Similarity	NPC193779
0.8418	Intermediate Similarity	NPC87295
0.8412	Intermediate Similarity	NPC471922
0.8412	Intermediate Similarity	NPC114550
0.8412	Intermediate Similarity	NPC292712
0.8412	Intermediate Similarity	NPC129930
0.8412	Intermediate Similarity	NPC474075
0.8412	Intermediate Similarity	NPC473697
0.8412	Intermediate Similarity	NPC38438
0.8412	Intermediate Similarity	NPC471920
0.8412	Intermediate Similarity	NPC20114
0.8412	Intermediate Similarity	NPC312006
0.8412	Intermediate Similarity	NPC471921
0.8397	Intermediate Similarity	NPC210354
0.8397	Intermediate Similarity	NPC151423
0.8397	Intermediate Similarity	NPC40237
0.8397	Intermediate Similarity	NPC176586
0.8395	Intermediate Similarity	NPC308555
0.8395	Intermediate Similarity	NPC68882
0.8395	Intermediate Similarity	NPC475141
0.8377	Intermediate Similarity	NPC865
0.8375	Intermediate Similarity	NPC177476
0.8375	Intermediate Similarity	NPC127827
0.8375	Intermediate Similarity	NPC262455
0.8373	Intermediate Similarity	NPC34376
0.8372	Intermediate Similarity	NPC473713
0.8372	Intermediate Similarity	NPC472723
0.8365	Intermediate Similarity	NPC153620
0.8365	Intermediate Similarity	NPC24257
0.8354	Intermediate Similarity	NPC155063
0.8354	Intermediate Similarity	NPC109765
0.8344	Intermediate Similarity	NPC474288
0.8344	Intermediate Similarity	NPC478213
0.8344	Intermediate Similarity	NPC57211
0.8343	Intermediate Similarity	NPC42230
0.8333	Intermediate Similarity	NPC267091
0.8333	Intermediate Similarity	NPC53680
0.8333	Intermediate Similarity	NPC208797
0.8333	Intermediate Similarity	NPC475953
0.8324	Intermediate Similarity	NPC35266
0.8323	Intermediate Similarity	NPC475722
0.8323	Intermediate Similarity	NPC478199
0.8323	Intermediate Similarity	NPC470916
0.8323	Intermediate Similarity	NPC198796
0.8313	Intermediate Similarity	NPC150943
0.8313	Intermediate Similarity	NPC63061
0.8313	Intermediate Similarity	NPC91634
0.8313	Intermediate Similarity	NPC119910
0.8313	Intermediate Similarity	NPC268718
0.8312	Intermediate Similarity	NPC143895
0.8303	Intermediate Similarity	NPC181168
0.8303	Intermediate Similarity	NPC115281
0.8303	Intermediate Similarity	NPC258644
0.8303	Intermediate Similarity	NPC163527
0.8303	Intermediate Similarity	NPC202495
0.8303	Intermediate Similarity	NPC143328
0.8302	Intermediate Similarity	NPC213482
0.8302	Intermediate Similarity	NPC296575
0.8301	Intermediate Similarity	NPC145722
0.8301	Intermediate Similarity	NPC256776
0.8301	Intermediate Similarity	NPC185680
0.8293	Intermediate Similarity	NPC222185
0.8293	Intermediate Similarity	NPC254163
0.8293	Intermediate Similarity	NPC117154
0.8291	Intermediate Similarity	NPC191158
0.8291	Intermediate Similarity	NPC218841

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 NPC280778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	958
0.2-0.3	1715
0.3-0.4	2729
0.4-0.5	1852
0.5-0.6	970
0.6-0.7	446
0.7-0.8	102
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8782	High Similarity	NPD6980	Clinical (unspecified phase)
0.8509	High Similarity	NPD37	Approved
0.8466	Intermediate Similarity	NPD4965	Approved
0.8466	Intermediate Similarity	NPD4967	Phase 2
0.8466	Intermediate Similarity	NPD4966	Approved
0.8373	Intermediate Similarity	NPD7199	Phase 2
0.8364	Intermediate Similarity	NPD6234	Discontinued
0.8274	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5844	Phase 1
0.8107	Intermediate Similarity	NPD6232	Discontinued
0.807	Intermediate Similarity	NPD7473	Discontinued
0.8024	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD3818	Discontinued
0.8023	Intermediate Similarity	NPD7228	Approved
0.8012	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5494	Approved
0.7857	Intermediate Similarity	NPD3817	Phase 2
0.7841	Intermediate Similarity	NPD7240	Approved
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7685	Pre-registration
0.7736	Intermediate Similarity	NPD3748	Approved
0.7727	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD7819	Suspended
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.767	Intermediate Similarity	NPD7054	Approved
0.7644	Intermediate Similarity	NPD3926	Phase 2
0.7637	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD1934	Approved
0.7627	Intermediate Similarity	NPD7472	Approved
0.7616	Intermediate Similarity	NPD919	Approved
0.76	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6166	Phase 2
0.76	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD3882	Suspended
0.7486	Intermediate Similarity	NPD6797	Phase 2
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5006	Approved
0.7474	Intermediate Similarity	NPD5005	Approved
0.7469	Intermediate Similarity	NPD2796	Approved
0.7457	Intermediate Similarity	NPD3749	Approved
0.7451	Intermediate Similarity	NPD3705	Approved
0.7444	Intermediate Similarity	NPD7251	Discontinued
0.7443	Intermediate Similarity	NPD5242	Approved
0.7416	Intermediate Similarity	NPD3751	Discontinued
0.7399	Intermediate Similarity	NPD7768	Phase 2
0.7396	Intermediate Similarity	NPD1653	Approved
0.7386	Intermediate Similarity	NPD7229	Phase 3
0.7386	Intermediate Similarity	NPD3787	Discontinued
0.7384	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD2801	Approved
0.7384	Intermediate Similarity	NPD8455	Phase 2
0.7378	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7411	Suspended
0.7366	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6799	Approved
0.7363	Intermediate Similarity	NPD8312	Approved
0.7363	Intermediate Similarity	NPD8313	Approved
0.7362	Intermediate Similarity	NPD2438	Suspended
0.7358	Intermediate Similarity	NPD3764	Approved
0.7356	Intermediate Similarity	NPD7075	Discontinued
0.7354	Intermediate Similarity	NPD4420	Approved
0.7353	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5402	Approved
0.7341	Intermediate Similarity	NPD5353	Approved
0.733	Intermediate Similarity	NPD1247	Approved
0.733	Intermediate Similarity	NPD8127	Discontinued
0.733	Intermediate Similarity	NPD6959	Discontinued
0.7326	Intermediate Similarity	NPD6801	Discontinued
0.7322	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2533	Approved
0.7321	Intermediate Similarity	NPD2532	Approved
0.7321	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD6599	Discontinued
0.731	Intermediate Similarity	NPD4380	Phase 2
0.7254	Intermediate Similarity	NPD7680	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7241	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5403	Approved
0.7235	Intermediate Similarity	NPD920	Approved
0.7229	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5401	Approved
0.7207	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4628	Phase 3
0.7186	Intermediate Similarity	NPD7003	Approved
0.7182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6273	Approved
0.7168	Intermediate Similarity	NPD6385	Approved
0.7168	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD1511	Approved
0.716	Intermediate Similarity	NPD2979	Phase 3
0.7157	Intermediate Similarity	NPD8151	Discontinued
0.7152	Intermediate Similarity	NPD2935	Discontinued
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1243	Approved
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7118	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD230	Phase 1
0.711	Intermediate Similarity	NPD7028	Phase 2
0.7108	Intermediate Similarity	NPD7266	Discontinued
0.7101	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1510	Phase 2
0.7083	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3027	Phase 3
0.7076	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1512	Approved
0.7066	Intermediate Similarity	NPD1549	Phase 2
0.7052	Intermediate Similarity	NPD3226	Approved
0.7037	Intermediate Similarity	NPD6798	Discontinued
0.7027	Intermediate Similarity	NPD7549	Discontinued
0.7024	Intermediate Similarity	NPD6674	Discontinued
0.7018	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6355	Discontinued
0.7012	Intermediate Similarity	NPD447	Suspended
0.7006	Intermediate Similarity	NPD1281	Approved
0.7006	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2798	Approved
0.699	Remote Similarity	NPD7435	Discontinued
0.6982	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4110	Phase 3
0.6981	Remote Similarity	NPD1876	Approved
0.698	Remote Similarity	NPD7930	Approved
0.6957	Remote Similarity	NPD3018	Phase 2
0.6951	Remote Similarity	NPD1613	Approved
0.6951	Remote Similarity	NPD4307	Phase 2
0.6951	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1240	Approved
0.6949	Remote Similarity	NPD4288	Approved
0.6946	Remote Similarity	NPD1551	Phase 2
0.6923	Remote Similarity	NPD6781	Approved
0.6923	Remote Similarity	NPD6777	Approved
0.6923	Remote Similarity	NPD6779	Approved
0.6923	Remote Similarity	NPD6776	Approved
0.6923	Remote Similarity	NPD6778	Approved
0.6923	Remote Similarity	NPD6780	Approved
0.6923	Remote Similarity	NPD6782	Approved
0.6919	Remote Similarity	NPD7999	Approved
0.6915	Remote Similarity	NPD7783	Phase 2
0.6915	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4908	Phase 1
0.691	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2346	Discontinued
0.6903	Remote Similarity	NPD5536	Phase 2
0.689	Remote Similarity	NPD6233	Phase 2
0.6886	Remote Similarity	NPD2799	Discontinued
0.6882	Remote Similarity	NPD7039	Approved
0.6882	Remote Similarity	NPD7038	Approved
0.6879	Remote Similarity	NPD17	Approved
0.6875	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1283	Approved
0.6875	Remote Similarity	NPD6873	Phase 2
0.6872	Remote Similarity	NPD6971	Discontinued
0.6871	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7870	Phase 2
0.6869	Remote Similarity	NPD7871	Phase 2
0.6867	Remote Similarity	NPD1607	Approved
0.6863	Remote Similarity	NPD5283	Phase 1
0.6855	Remote Similarity	NPD2981	Phase 2
0.6853	Remote Similarity	NPD6823	Phase 2
0.6845	Remote Similarity	NPD2531	Phase 2
0.6845	Remote Similarity	NPD5406	Approved
0.6845	Remote Similarity	NPD5404	Approved
0.6845	Remote Similarity	NPD5408	Approved
0.6845	Remote Similarity	NPD5405	Approved
0.6832	Remote Similarity	NPD3266	Approved
0.6832	Remote Similarity	NPD3267	Approved
0.6832	Remote Similarity	NPD2797	Approved
0.6829	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7097	Phase 1
0.6821	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD7698	Approved
0.6818	Remote Similarity	NPD7697	Approved
0.6815	Remote Similarity	NPD5691	Approved
0.6813	Remote Similarity	NPD2983	Phase 2
0.6813	Remote Similarity	NPD2982	Phase 2
0.6813	Remote Similarity	NPD5711	Approved
0.6813	Remote Similarity	NPD5710	Approved
0.681	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6746	Phase 2
0.6789	Remote Similarity	NPD8150	Discontinued
0.6788	Remote Similarity	NPD8032	Phase 2
0.6786	Remote Similarity	NPD4308	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