NPASS Compound

Structure

NPC7213 OpenBabel07101719522D 54 60 0 0 1 0 0 0 0 0999 V2000 -4.8973 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5446 -4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2679 5.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5665 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9703 -2.4680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7679 4.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2679 3.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7679 2.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2321 2.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7321 3.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2679 5.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6394 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2679 3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2679 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2321 4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 5 38 1 0 0 0 0 7 8 1 0 0 0 0 7 20 2 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 28 1 0 0 0 0 12 40 1 0 0 0 0 13 14 1 0 0 0 0 13 38 1 0 0 0 0 15 23 1 0 0 0 0 15 39 1 0 0 0 0 16 42 1 0 0 0 0 17 24 1 0 0 0 0 17 51 1 0 0 0 0 18 40 1 0 0 0 0 18 41 1 0 0 0 0 19 37 1 0 0 0 0 19 52 1 0 0 0 0 21 3 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 43 1 6 0 0 0 23 29 1 0 0 0 0 23 44 1 1 0 0 0 24 30 1 0 0 0 0 24 45 1 6 0 0 0 25 16 1 1 0 0 0 25 31 1 0 0 0 0 25 53 1 0 0 0 0 26 37 1 1 0 0 0 26 40 1 0 0 0 0 27 39 1 6 0 0 0 27 41 1 0 0 0 0 28 37 1 1 0 0 0 28 54 1 0 0 0 0 29 38 1 1 0 0 0 30 33 1 0 0 0 0 30 46 1 6 0 0 0 31 32 1 0 0 0 0 31 47 1 6 0 0 0 32 34 1 0 0 0 0 32 48 1 1 0 0 0 33 35 1 0 0 0 0 33 49 1 1 0 0 0 34 36 1 0 0 0 0 34 50 1 6 0 0 0 35 51 1 0 0 0 0 35 54 1 6 0 0 0 36 52 1 1 0 0 0 36 53 1 0 0 0 0 37 4 1 1 0 0 0 38 39 1 1 0 0 0 39 6 1 6 0 0 0 40 41 1 6 0 0 0 41 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	768.47
Volume:	769.433
LogP:	2.505
LogD:	2.802
LogS:	-3.799
# Rotatable Bonds:	10
TPSA:	218.99
# H-Bond Aceptor:	13
# H-Bond Donor:	9
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	6.801
Fsp3:	0.951
Lipinski Rule-of-5:	Rejected
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:	-5.94
MDCK Permeability:	2.1737600036431104e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.95
20% Bioavailability (F20%):	0.726
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	68.41602325439453%
Volume Distribution (VD):	0.254
Pgp-substrate:	10.054619789123535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.844
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.481
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	0.612
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.262
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.56
Skin Sensitization:	0.925
Carcinogencity:	0.123
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC7213

Natural Product ID:	NPC7213
*Common Name:**	Thalicoside A2
IUPAC Name:	n.a.
Synonyms:	thalicoside A2
Standard InCHIKey:	DQRIDXWUXLELEC-DLHBQLSASA-N
Standard InCHI:	InChI=1S/C41H68O13/c1-20(2)7-8-22(43)21(3)29-23(44)15-39(6)27-10-9-26-37(4,19-52-36-34(50)32(48)31(47)25(16-42)53-36)28(54-35-33(49)30(46)24(45)17-51-35)11-12-40(26)18-41(27,40)14-13-38(29,39)5/h7,21-36,42-50H,8-19H2,1-6H3/t21-,22+,23+,24+,25-,26+,27+,28+,29+,30+,31-,32+,33-,34-,35+,36-,37+,38-,39+,40-,41+/m1/s1
SMILES:	CC(=CC[C@@H]([C@@H](C)[C@H]1[C@H](C[C@@]2(C)[C@@H]3CC[C@H]4[C@](C)(CO[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446322
PubChem CID:	21606556
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924164]
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11635	Thalictrum minus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11635	Thalictrum minus	Species	Ranunculaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	78.7	%	PMID[507785]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	45.7	%	PMID[507785]

☑ 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 NPC7213 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	305
0.1-0.2	2177
0.2-0.3	6865
0.3-0.4	13972
0.4-0.5	8473
0.5-0.6	5342
0.6-0.7	3218
0.7-0.8	1449
0.8-0.85	585
0.85-0.9	225
0.9-0.95	84
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.97	High Similarity	NPC473469
0.96	High Similarity	NPC242748
0.9495	High Similarity	NPC312553
0.9495	High Similarity	NPC159036
0.9495	High Similarity	NPC288694
0.9406	High Similarity	NPC473923
0.9406	High Similarity	NPC473476
0.94	High Similarity	NPC155010
0.94	High Similarity	NPC16573
0.94	High Similarity	NPC286969
0.94	High Similarity	NPC472252
0.94	High Similarity	NPC16520
0.94	High Similarity	NPC131479
0.94	High Similarity	NPC211879
0.94	High Similarity	NPC31907
0.94	High Similarity	NPC120123
0.94	High Similarity	NPC245280
0.94	High Similarity	NPC189852
0.94	High Similarity	NPC473020
0.94	High Similarity	NPC114874
0.94	High Similarity	NPC8039
0.94	High Similarity	NPC157659
0.9327	High Similarity	NPC114188
0.932	High Similarity	NPC476835
0.9307	High Similarity	NPC470885
0.9307	High Similarity	NPC165033
0.9307	High Similarity	NPC273879
0.9307	High Similarity	NPC221562
0.9307	High Similarity	NPC187400
0.93	High Similarity	NPC136816
0.9293	High Similarity	NPC473200
0.9293	High Similarity	NPC7341
0.9223	High Similarity	NPC476541
0.9223	High Similarity	NPC476540
0.9223	High Similarity	NPC476539
0.9223	High Similarity	NPC476538
0.9216	High Similarity	NPC152584
0.9216	High Similarity	NPC208594
0.9216	High Similarity	NPC474569
0.9216	High Similarity	NPC181845
0.9216	High Similarity	NPC208477
0.9216	High Similarity	NPC127801
0.9216	High Similarity	NPC160816
0.9216	High Similarity	NPC194842
0.9216	High Similarity	NPC269627
0.9216	High Similarity	NPC69737
0.9208	High Similarity	NPC473198
0.92	High Similarity	NPC4831
0.92	High Similarity	NPC47566
0.92	High Similarity	NPC472023
0.92	High Similarity	NPC31346
0.92	High Similarity	NPC129372
0.92	High Similarity	NPC160734
0.92	High Similarity	NPC88000
0.92	High Similarity	NPC309425
0.9192	High Similarity	NPC280825
0.9192	High Similarity	NPC234287
0.9151	High Similarity	NPC476693
0.9143	High Similarity	NPC472987
0.9143	High Similarity	NPC473021
0.9143	High Similarity	NPC197231
0.9135	High Similarity	NPC477026
0.9135	High Similarity	NPC70204
0.9135	High Similarity	NPC306131
0.9135	High Similarity	NPC477027
0.9135	High Similarity	NPC475670
0.9126	High Similarity	NPC181467
0.9126	High Similarity	NPC283829
0.9126	High Similarity	NPC14946
0.9126	High Similarity	NPC470432
0.9126	High Similarity	NPC234160
0.9126	High Similarity	NPC94272
0.9126	High Similarity	NPC230507
0.9126	High Similarity	NPC208650
0.9126	High Similarity	NPC305423
0.9126	High Similarity	NPC113044
0.9126	High Similarity	NPC14704
0.9126	High Similarity	NPC161676
0.9126	High Similarity	NPC63368
0.9126	High Similarity	NPC231340
0.9126	High Similarity	NPC190395
0.9118	High Similarity	NPC475365
0.9118	High Similarity	NPC475521
0.9118	High Similarity	NPC312774
0.9109	High Similarity	NPC272015
0.91	High Similarity	NPC282669
0.9091	High Similarity	NPC76486
0.9057	High Similarity	NPC19888
0.9038	High Similarity	NPC295980
0.9038	High Similarity	NPC98696
0.9038	High Similarity	NPC472988
0.9038	High Similarity	NPC476513
0.9038	High Similarity	NPC220427
0.9038	High Similarity	NPC6931
0.9038	High Similarity	NPC38217
0.9038	High Similarity	NPC472896
0.9038	High Similarity	NPC159005
0.9038	High Similarity	NPC180183
0.9038	High Similarity	NPC246124
0.9038	High Similarity	NPC472897
0.9029	High Similarity	NPC309448
0.9029	High Similarity	NPC472899
0.9029	High Similarity	NPC472900
0.9029	High Similarity	NPC472898
0.902	High Similarity	NPC213190
0.8972	High Similarity	NPC144068
0.8962	High Similarity	NPC475247
0.8962	High Similarity	NPC13190
0.8962	High Similarity	NPC294129
0.8962	High Similarity	NPC476547
0.8952	High Similarity	NPC125361
0.8952	High Similarity	NPC95051
0.8952	High Similarity	NPC43976
0.8952	High Similarity	NPC472901
0.8952	High Similarity	NPC249265
0.8952	High Similarity	NPC477809
0.8952	High Similarity	NPC46190
0.8952	High Similarity	NPC22779
0.8952	High Similarity	NPC6806
0.8952	High Similarity	NPC208383
0.8952	High Similarity	NPC248746
0.8952	High Similarity	NPC296761
0.8952	High Similarity	NPC224098
0.8952	High Similarity	NPC51925
0.8952	High Similarity	NPC150372
0.8952	High Similarity	NPC218571
0.8952	High Similarity	NPC194207
0.8952	High Similarity	NPC232054
0.8952	High Similarity	NPC40440
0.8952	High Similarity	NPC84956
0.8952	High Similarity	NPC42482
0.8952	High Similarity	NPC73243
0.8952	High Similarity	NPC475550
0.8952	High Similarity	NPC309278
0.8952	High Similarity	NPC475333
0.8952	High Similarity	NPC470433
0.8952	High Similarity	NPC171073
0.8952	High Similarity	NPC102016
0.8952	High Similarity	NPC302057
0.8952	High Similarity	NPC300557
0.8952	High Similarity	NPC244086
0.8952	High Similarity	NPC154085
0.8942	High Similarity	NPC226642
0.8932	High Similarity	NPC75608
0.8911	High Similarity	NPC91497
0.89	High Similarity	NPC473890
0.89	High Similarity	NPC243728
0.8889	High Similarity	NPC477810
0.8879	High Similarity	NPC263359
0.8879	High Similarity	NPC244431
0.8879	High Similarity	NPC210569
0.8879	High Similarity	NPC31896
0.8879	High Similarity	NPC112274
0.8879	High Similarity	NPC32361
0.8879	High Similarity	NPC475312
0.8868	High Similarity	NPC224314
0.8868	High Similarity	NPC23808
0.8868	High Similarity	NPC141433
0.8868	High Similarity	NPC269297
0.8868	High Similarity	NPC87998
0.8868	High Similarity	NPC247037
0.8868	High Similarity	NPC472717
0.8868	High Similarity	NPC222202
0.8868	High Similarity	NPC477811
0.8857	High Similarity	NPC128123
0.8857	High Similarity	NPC475634
0.8846	High Similarity	NPC473199
0.8846	High Similarity	NPC26798
0.8824	High Similarity	NPC263756
0.8824	High Similarity	NPC117714
0.8818	High Similarity	NPC476692
0.8818	High Similarity	NPC476691
0.8818	High Similarity	NPC472080
0.8812	High Similarity	NPC158088
0.8807	High Similarity	NPC212660
0.88	High Similarity	NPC472989
0.8796	High Similarity	NPC307642
0.8796	High Similarity	NPC79900
0.8796	High Similarity	NPC51154
0.8796	High Similarity	NPC476546
0.8785	High Similarity	NPC124677
0.8785	High Similarity	NPC470748
0.8785	High Similarity	NPC477028
0.8785	High Similarity	NPC477032
0.8785	High Similarity	NPC13193
0.8785	High Similarity	NPC65167
0.8785	High Similarity	NPC472715
0.8774	High Similarity	NPC157530
0.8774	High Similarity	NPC14630
0.8774	High Similarity	NPC474573
0.8774	High Similarity	NPC250089
0.8762	High Similarity	NPC78034
0.875	High Similarity	NPC93352
0.875	High Similarity	NPC109792
0.875	High Similarity	NPC57065
0.875	High Similarity	NPC54521
0.875	High Similarity	NPC471111
0.8738	High Similarity	NPC213674
0.8738	High Similarity	NPC256133
0.8738	High Similarity	NPC76497

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 NPC7213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	2302
0.2-0.3	4336
0.3-0.4	1476
0.4-0.5	432
0.5-0.6	249
0.6-0.7	93
0.7-0.8	14
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8584	High Similarity	NPD8033	Approved
0.8496	Intermediate Similarity	NPD8294	Approved
0.8496	Intermediate Similarity	NPD8377	Approved
0.8421	Intermediate Similarity	NPD8378	Approved
0.8421	Intermediate Similarity	NPD8296	Approved
0.8421	Intermediate Similarity	NPD8335	Approved
0.8421	Intermediate Similarity	NPD8380	Approved
0.8421	Intermediate Similarity	NPD8379	Approved
0.8158	Intermediate Similarity	NPD7327	Approved
0.8158	Intermediate Similarity	NPD7328	Approved
0.8137	Intermediate Similarity	NPD8171	Discontinued
0.8087	Intermediate Similarity	NPD7516	Approved
0.7909	Intermediate Similarity	NPD6412	Phase 2
0.7807	Intermediate Similarity	NPD8133	Approved
0.7797	Intermediate Similarity	NPD7503	Approved
0.7686	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.746	Intermediate Similarity	NPD8449	Approved
0.7458	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD8450	Suspended
0.7377	Intermediate Similarity	NPD8328	Phase 3
0.73	Intermediate Similarity	NPD7525	Registered
0.728	Intermediate Similarity	NPD7736	Approved
0.7154	Intermediate Similarity	NPD6370	Approved
0.7129	Intermediate Similarity	NPD6928	Phase 2
0.7069	Intermediate Similarity	NPD6686	Approved
0.7063	Intermediate Similarity	NPD8293	Discontinued
0.703	Intermediate Similarity	NPD7645	Phase 2
0.6992	Remote Similarity	NPD6054	Approved
0.6992	Remote Similarity	NPD6059	Approved
0.6981	Remote Similarity	NPD7524	Approved
0.6964	Remote Similarity	NPD7638	Approved
0.6903	Remote Similarity	NPD7640	Approved
0.6903	Remote Similarity	NPD7639	Approved
0.69	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8297	Approved
0.6833	Remote Similarity	NPD6882	Approved
0.6825	Remote Similarity	NPD6067	Discontinued
0.68	Remote Similarity	NPD6016	Approved
0.68	Remote Similarity	NPD6942	Approved
0.68	Remote Similarity	NPD7339	Approved
0.68	Remote Similarity	NPD6015	Approved
0.6772	Remote Similarity	NPD7492	Approved
0.6763	Remote Similarity	NPD7625	Phase 1
0.6762	Remote Similarity	NPD6695	Phase 3
0.6748	Remote Similarity	NPD6009	Approved
0.6746	Remote Similarity	NPD5988	Approved
0.672	Remote Similarity	NPD6319	Approved
0.6719	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6639	Remote Similarity	NPD4632	Approved
0.661	Remote Similarity	NPD6675	Approved
0.661	Remote Similarity	NPD5739	Approved
0.661	Remote Similarity	NPD6402	Approved
0.661	Remote Similarity	NPD7128	Approved
0.6583	Remote Similarity	NPD6372	Approved
0.6583	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD8034	Phase 2
0.6577	Remote Similarity	NPD8035	Phase 2
0.6569	Remote Similarity	NPD6933	Approved
0.6562	Remote Similarity	NPD7604	Phase 2
0.6538	Remote Similarity	NPD6929	Approved
0.6518	Remote Similarity	NPD6399	Phase 3
0.65	Remote Similarity	NPD6881	Approved
0.65	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD7320	Approved
0.6489	Remote Similarity	NPD6033	Approved
0.648	Remote Similarity	NPD7115	Discovery
0.6476	Remote Similarity	NPD6930	Phase 2
0.6476	Remote Similarity	NPD6931	Approved
0.6475	Remote Similarity	NPD6650	Approved
0.6475	Remote Similarity	NPD8130	Phase 1
0.6475	Remote Similarity	NPD6649	Approved
0.6471	Remote Similarity	NPD6008	Approved
0.646	Remote Similarity	NPD7748	Approved
0.6435	Remote Similarity	NPD7902	Approved
0.6435	Remote Similarity	NPD4755	Approved
0.6417	Remote Similarity	NPD5701	Approved
0.6417	Remote Similarity	NPD5697	Approved
0.6415	Remote Similarity	NPD6902	Approved
0.641	Remote Similarity	NPD4159	Approved
0.6404	Remote Similarity	NPD7991	Discontinued
0.6393	Remote Similarity	NPD7290	Approved
0.6393	Remote Similarity	NPD4634	Approved
0.6393	Remote Similarity	NPD7102	Approved
0.6393	Remote Similarity	NPD6883	Approved
0.6389	Remote Similarity	NPD4786	Approved
0.6373	Remote Similarity	NPD6926	Approved
0.6373	Remote Similarity	NPD4785	Approved
0.6373	Remote Similarity	NPD6924	Approved
0.6373	Remote Similarity	NPD4784	Approved
0.6372	Remote Similarity	NPD4202	Approved
0.6356	Remote Similarity	NPD7632	Discontinued
0.6346	Remote Similarity	NPD6932	Approved
0.6346	Remote Similarity	NPD6925	Approved
0.6346	Remote Similarity	NPD5776	Phase 2
0.6341	Remote Similarity	NPD6847	Approved
0.6341	Remote Similarity	NPD6869	Approved
0.6341	Remote Similarity	NPD6617	Approved
0.6341	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD3168	Discontinued
0.6337	Remote Similarity	NPD4243	Approved
0.633	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4700	Approved
0.6325	Remote Similarity	NPD5285	Approved
0.6325	Remote Similarity	NPD4696	Approved
0.6325	Remote Similarity	NPD5286	Approved
0.6321	Remote Similarity	NPD4748	Discontinued
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.63	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6083	Phase 2
0.6293	Remote Similarity	NPD6084	Phase 2
0.6286	Remote Similarity	NPD7145	Approved
0.6283	Remote Similarity	NPD7515	Phase 2
0.6283	Remote Similarity	NPD7087	Discontinued
0.6279	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD5328	Approved
0.6239	Remote Similarity	NPD4225	Approved
0.623	Remote Similarity	NPD6011	Approved
0.6226	Remote Similarity	NPD6683	Phase 2
0.6218	Remote Similarity	NPD5211	Phase 2
0.6218	Remote Similarity	NPD5225	Approved
0.6218	Remote Similarity	NPD5224	Approved
0.6218	Remote Similarity	NPD5226	Approved
0.6218	Remote Similarity	NPD4633	Approved
0.6214	Remote Similarity	NPD1811	Approved
0.6214	Remote Similarity	NPD1810	Approved
0.6212	Remote Similarity	NPD6336	Discontinued
0.621	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3667	Approved
0.6198	Remote Similarity	NPD4767	Approved
0.6198	Remote Similarity	NPD4768	Approved
0.6182	Remote Similarity	NPD6893	Approved
0.6179	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7150	Approved
0.6176	Remote Similarity	NPD7151	Approved
0.6176	Remote Similarity	NPD7152	Approved
0.6174	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7900	Approved
0.6168	Remote Similarity	NPD7514	Phase 3
0.6168	Remote Similarity	NPD7509	Discontinued
0.6167	Remote Similarity	NPD5175	Approved
0.6167	Remote Similarity	NPD5174	Approved
0.6161	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7637	Suspended
0.614	Remote Similarity	NPD6079	Approved
0.6139	Remote Similarity	NPD6923	Approved
0.6139	Remote Similarity	NPD6922	Approved
0.6134	Remote Similarity	NPD5344	Discontinued
0.6134	Remote Similarity	NPD5223	Approved
0.6126	Remote Similarity	NPD3618	Phase 1
0.6121	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5141	Approved
0.6106	Remote Similarity	NPD6051	Approved
0.6106	Remote Similarity	NPD4753	Phase 2
0.6098	Remote Similarity	NPD4729	Approved
0.6098	Remote Similarity	NPD4730	Approved
0.6091	Remote Similarity	NPD3666	Approved
0.6091	Remote Similarity	NPD3665	Phase 1
0.6091	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD7144	Approved
0.6078	Remote Similarity	NPD7143	Approved
0.6033	Remote Similarity	NPD4754	Approved
0.6029	Remote Similarity	NPD5956	Approved
0.6019	Remote Similarity	NPD7332	Phase 2
0.6016	Remote Similarity	NPD6274	Approved
0.6016	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD5250	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD5275	Approved
0.6	Remote Similarity	NPD5249	Phase 3
0.6	Remote Similarity	NPD5248	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5247	Approved
0.6	Remote Similarity	NPD5251	Approved
0.6	Remote Similarity	NPD4190	Phase 3
0.5983	Remote Similarity	NPD5695	Phase 3
0.5982	Remote Similarity	NPD5330	Approved
0.5982	Remote Similarity	NPD7521	Approved
0.5982	Remote Similarity	NPD6684	Approved
0.5982	Remote Similarity	NPD6409	Approved
0.5982	Remote Similarity	NPD7146	Approved
0.5982	Remote Similarity	NPD7334	Approved
0.5968	Remote Similarity	NPD5128	Approved
0.5968	Remote Similarity	NPD8174	Phase 2
0.5968	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD5696	Approved

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