NPASS Compound

Structure

NPC286612 OpenBabel07101718202D 33 36 0 0 1 0 0 0 0 0999 V2000 8.2473 0.1830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1048 -1.1528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2473 0.1830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6238 3.1578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0152 3.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7473 1.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2832 4.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1492 3.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1492 0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2832 1.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4171 3.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7473 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8812 2.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8812 0.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -1.6279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1583 1.5831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1062 -1.2051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0152 1.0490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2832 2.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1492 2.5490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0523 -0.9986 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0183 -1.2574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5629 -0.4188 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9336 0.3584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7473 1.0490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4171 2.5490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0152 2.0490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5684 -2.6156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6522 -2.0961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3766 -2.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1924 1.3243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5615 -0.3664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 17 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 26 1 0 0 0 0 16 31 1 0 0 0 0 17 29 2 0 0 0 0 17 32 1 0 0 0 0 18 27 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 6 0 0 0 21 15 1 6 0 0 0 21 22 1 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 22 30 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 31 1 1 0 0 0 24 33 1 0 0 0 0 25 3 1 1 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.3
Volume:	486.154
LogP:	4.64
LogD:	3.769
LogS:	-4.265
# Rotatable Bonds:	7
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	5.124
Fsp3:	0.815
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:	-4.972
MDCK Permeability:	6.864514489279827e-06
Pgp-inhibitor:	0.58
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.143
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	81.45250701904297%
Volume Distribution (VD):	1.678
Pgp-substrate:	20.564233779907227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.647
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.708
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.94
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	2.191
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.442
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.253
Carcinogencity:	0.349
Eye Corrosion:	0.009
Eye Irritation:	0.021
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC286612

Natural Product ID:	NPC286612
*Common Name:**	Sagittine D
IUPAC Name:	[(2R,3R,4S,5S)-2-[[(1S,4aR,4bS,7S,8aS)-7-ethenyl-1,4b,7-trimethyl-3,4,4a,5,6,8,8a,9-octahydro-2H-phenanthren-1-yl]methoxy]-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] acetate
Synonyms:	sagittine D
Standard InCHIKey:	JRSFSLRWEYOFKG-WJSBELDJSA-N
Standard InCHI:	InChI=1S/C27H42O6/c1-6-25(3)12-13-27(5)18(14-25)9-10-19-20(27)8-7-11-26(19,4)16-31-24-23(32-17(2)29)22(30)21(15-28)33-24/h6,10,18,20-24,28,30H,1,7-9,11-16H2,2-5H3/t18-,20-,21-,22-,23+,24+,25-,26+,27-/m0/s1
SMILES:	OC[C@@H]1O[C@H]([C@@H]([C@H]1O)OC(=O)C)OC[C@@]1(C)CCC[C@H]2C1=CC[C@@H]1[C@]2(C)CC[C@](C1)(C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481067
PubChem CID:	11641229
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499326]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	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
NPT1655	Organism	Actinobacillus actinomycetemcomitans	Aggregatibacter actinomycetemcomitans	MIC	=	250.0	ug.mL-1	PMID[558750]
NPT4399	Organism	Actinomyces naeslundii	Actinomyces naeslundii	MIC	=	125.0	ug.mL-1	PMID[558750]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	125.0	ug.mL-1	PMID[558750]

☑ 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 NPC286612 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	176
0.1-0.2	1085
0.2-0.3	4614
0.3-0.4	12568
0.4-0.5	9326
0.5-0.6	6333
0.6-0.7	5900
0.7-0.8	2459
0.8-0.85	191
0.85-0.9	37
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC230347
1.0	High Similarity	NPC275310
0.9545	High Similarity	NPC159876
0.9432	High Similarity	NPC473058
0.9255	High Similarity	NPC21064
0.9255	High Similarity	NPC121072
0.9158	High Similarity	NPC154452
0.9022	High Similarity	NPC211238
0.8936	High Similarity	NPC239547
0.8936	High Similarity	NPC155319
0.8936	High Similarity	NPC309503
0.8936	High Similarity	NPC96597
0.8936	High Similarity	NPC125551
0.8936	High Similarity	NPC91197
0.8842	High Similarity	NPC477928
0.883	High Similarity	NPC207617
0.8776	High Similarity	NPC31430
0.8776	High Similarity	NPC85593
0.8646	High Similarity	NPC158088
0.8617	High Similarity	NPC305160
0.8617	High Similarity	NPC178949
0.8617	High Similarity	NPC96736
0.86	High Similarity	NPC293512
0.8586	High Similarity	NPC470061
0.8586	High Similarity	NPC470043
0.8586	High Similarity	NPC470058
0.8586	High Similarity	NPC470057
0.8586	High Similarity	NPC470064
0.8586	High Similarity	NPC470062
0.8586	High Similarity	NPC470059
0.8586	High Similarity	NPC470060
0.8571	High Similarity	NPC470571
0.8542	High Similarity	NPC98112
0.8542	High Similarity	NPC473890
0.8542	High Similarity	NPC243728
0.8515	High Similarity	NPC128795
0.8515	High Similarity	NPC295980
0.8515	High Similarity	NPC295389
0.8515	High Similarity	NPC48548
0.8515	High Similarity	NPC217921
0.8515	High Similarity	NPC135015
0.8511	High Similarity	NPC67398
0.8511	High Similarity	NPC474792
0.8511	High Similarity	NPC474835
0.8511	High Similarity	NPC91654
0.85	High Similarity	NPC470056
0.85	High Similarity	NPC470055
0.85	High Similarity	NPC470767
0.85	High Similarity	NPC470763
0.8495	Intermediate Similarity	NPC469403
0.8478	Intermediate Similarity	NPC263079
0.8469	Intermediate Similarity	NPC280991
0.8469	Intermediate Similarity	NPC267510
0.8454	Intermediate Similarity	NPC5358
0.8454	Intermediate Similarity	NPC216260
0.8444	Intermediate Similarity	NPC319238
0.8431	Intermediate Similarity	NPC316974
0.8431	Intermediate Similarity	NPC40728
0.8421	Intermediate Similarity	NPC72817
0.8421	Intermediate Similarity	NPC477927
0.8416	Intermediate Similarity	NPC88013
0.8416	Intermediate Similarity	NPC125423
0.8404	Intermediate Similarity	NPC302584
0.84	Intermediate Similarity	NPC470768
0.84	Intermediate Similarity	NPC100955
0.84	Intermediate Similarity	NPC121566
0.84	Intermediate Similarity	NPC173583
0.8384	Intermediate Similarity	NPC272015
0.8384	Intermediate Similarity	NPC471363
0.8384	Intermediate Similarity	NPC238397
0.8367	Intermediate Similarity	NPC228251
0.8367	Intermediate Similarity	NPC161527
0.8367	Intermediate Similarity	NPC219285
0.8367	Intermediate Similarity	NPC477972
0.8367	Intermediate Similarity	NPC20113
0.8367	Intermediate Similarity	NPC282669
0.8367	Intermediate Similarity	NPC469942
0.8367	Intermediate Similarity	NPC477971
0.8367	Intermediate Similarity	NPC477968
0.8351	Intermediate Similarity	NPC473555
0.8351	Intermediate Similarity	NPC278939
0.8351	Intermediate Similarity	NPC471770
0.835	Intermediate Similarity	NPC101450
0.835	Intermediate Similarity	NPC127153
0.8333	Intermediate Similarity	NPC311223
0.8317	Intermediate Similarity	NPC473199
0.8317	Intermediate Similarity	NPC95243
0.8317	Intermediate Similarity	NPC162033
0.8317	Intermediate Similarity	NPC63023
0.83	Intermediate Similarity	NPC7644
0.83	Intermediate Similarity	NPC474575
0.83	Intermediate Similarity	NPC7613
0.83	Intermediate Similarity	NPC127933
0.83	Intermediate Similarity	NPC475889
0.83	Intermediate Similarity	NPC134270
0.8298	Intermediate Similarity	NPC471370
0.8298	Intermediate Similarity	NPC471371
0.8286	Intermediate Similarity	NPC144068
0.8283	Intermediate Similarity	NPC470434
0.8283	Intermediate Similarity	NPC21568
0.8283	Intermediate Similarity	NPC285231
0.8269	Intermediate Similarity	NPC114188
0.8269	Intermediate Similarity	NPC470748
0.8265	Intermediate Similarity	NPC157739
0.8252	Intermediate Similarity	NPC206618
0.8242	Intermediate Similarity	NPC166279
0.8235	Intermediate Similarity	NPC283849
0.8235	Intermediate Similarity	NPC234160
0.8218	Intermediate Similarity	NPC201880
0.8218	Intermediate Similarity	NPC223741
0.8218	Intermediate Similarity	NPC264867
0.8218	Intermediate Similarity	NPC470321
0.8218	Intermediate Similarity	NPC473207
0.8218	Intermediate Similarity	NPC81567
0.8208	Intermediate Similarity	NPC477808
0.8191	Intermediate Similarity	NPC293044
0.819	Intermediate Similarity	NPC317460
0.819	Intermediate Similarity	NPC470025
0.819	Intermediate Similarity	NPC328074
0.819	Intermediate Similarity	NPC473125
0.819	Intermediate Similarity	NPC321272
0.8182	Intermediate Similarity	NPC317019
0.8182	Intermediate Similarity	NPC324598
0.8182	Intermediate Similarity	NPC473790
0.8182	Intermediate Similarity	NPC146188
0.8173	Intermediate Similarity	NPC119550
0.8173	Intermediate Similarity	NPC274507
0.8173	Intermediate Similarity	NPC316708
0.8163	Intermediate Similarity	NPC475032
0.8163	Intermediate Similarity	NPC240372
0.8163	Intermediate Similarity	NPC475033
0.8155	Intermediate Similarity	NPC38948
0.8155	Intermediate Similarity	NPC28198
0.8155	Intermediate Similarity	NPC177246
0.8155	Intermediate Similarity	NPC284807
0.8155	Intermediate Similarity	NPC476123
0.8155	Intermediate Similarity	NPC38217
0.8155	Intermediate Similarity	NPC472988
0.8144	Intermediate Similarity	NPC472189
0.8144	Intermediate Similarity	NPC471362
0.8144	Intermediate Similarity	NPC471372
0.8137	Intermediate Similarity	NPC181845
0.8137	Intermediate Similarity	NPC252296
0.8131	Intermediate Similarity	NPC63609
0.8131	Intermediate Similarity	NPC477031
0.8119	Intermediate Similarity	NPC99627
0.8119	Intermediate Similarity	NPC473129
0.8113	Intermediate Similarity	NPC474410
0.8113	Intermediate Similarity	NPC44298
0.8113	Intermediate Similarity	NPC290608
0.8113	Intermediate Similarity	NPC470027
0.8113	Intermediate Similarity	NPC40133
0.8113	Intermediate Similarity	NPC49413
0.8113	Intermediate Similarity	NPC473128
0.8113	Intermediate Similarity	NPC293658
0.81	Intermediate Similarity	NPC475617
0.81	Intermediate Similarity	NPC470054
0.8095	Intermediate Similarity	NPC297208
0.8095	Intermediate Similarity	NPC191763
0.8095	Intermediate Similarity	NPC211798
0.8095	Intermediate Similarity	NPC285410
0.8095	Intermediate Similarity	NPC473481
0.8095	Intermediate Similarity	NPC235841
0.8095	Intermediate Similarity	NPC263827
0.8095	Intermediate Similarity	NPC17791
0.8095	Intermediate Similarity	NPC108748
0.8095	Intermediate Similarity	NPC470026
0.8095	Intermediate Similarity	NPC250481
0.8095	Intermediate Similarity	NPC30397
0.809	Intermediate Similarity	NPC100906
0.8085	Intermediate Similarity	NPC309656
0.8081	Intermediate Similarity	NPC309493
0.8081	Intermediate Similarity	NPC234287
0.8081	Intermediate Similarity	NPC280825
0.8077	Intermediate Similarity	NPC237503
0.8077	Intermediate Similarity	NPC118225
0.8077	Intermediate Similarity	NPC125361
0.8077	Intermediate Similarity	NPC167383
0.8077	Intermediate Similarity	NPC57362
0.8077	Intermediate Similarity	NPC306746
0.8077	Intermediate Similarity	NPC246205
0.8077	Intermediate Similarity	NPC137917
0.8077	Intermediate Similarity	NPC127853
0.8077	Intermediate Similarity	NPC296761
0.8077	Intermediate Similarity	NPC51925
0.8077	Intermediate Similarity	NPC154085
0.8077	Intermediate Similarity	NPC204407
0.8077	Intermediate Similarity	NPC43976
0.8077	Intermediate Similarity	NPC265655
0.8065	Intermediate Similarity	NPC471369
0.8065	Intermediate Similarity	NPC470836
0.8061	Intermediate Similarity	NPC94905
0.8061	Intermediate Similarity	NPC90583
0.8061	Intermediate Similarity	NPC171598
0.8061	Intermediate Similarity	NPC8954
0.8058	Intermediate Similarity	NPC305423
0.8058	Intermediate Similarity	NPC226642
0.8058	Intermediate Similarity	NPC283829
0.8058	Intermediate Similarity	NPC472390
0.8058	Intermediate Similarity	NPC230507

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 NPC286612 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1299
0.2-0.3	4084
0.3-0.4	2409
0.4-0.5	691
0.5-0.6	247
0.6-0.7	216
0.7-0.8	56
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8058	Intermediate Similarity	NPD6412	Phase 2
0.7981	Intermediate Similarity	NPD6686	Approved
0.7611	Intermediate Similarity	NPD7503	Approved
0.757	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.7456	Intermediate Similarity	NPD8033	Approved
0.7434	Intermediate Similarity	NPD7516	Approved
0.74	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD8294	Approved
0.7368	Intermediate Similarity	NPD8377	Approved
0.7304	Intermediate Similarity	NPD8378	Approved
0.7304	Intermediate Similarity	NPD8380	Approved
0.7304	Intermediate Similarity	NPD8335	Approved
0.7304	Intermediate Similarity	NPD8379	Approved
0.7304	Intermediate Similarity	NPD8296	Approved
0.7257	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6370	Approved
0.7227	Intermediate Similarity	NPD7736	Approved
0.7212	Intermediate Similarity	NPD4225	Approved
0.7179	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD8133	Approved
0.7119	Intermediate Similarity	NPD7492	Approved
0.7113	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7524	Approved
0.7069	Intermediate Similarity	NPD6054	Approved
0.7065	Intermediate Similarity	NPD6942	Approved
0.7065	Intermediate Similarity	NPD7339	Approved
0.7059	Intermediate Similarity	NPD7507	Approved
0.7059	Intermediate Similarity	NPD6616	Approved
0.7054	Intermediate Similarity	NPD6882	Approved
0.7048	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD7078	Approved
0.6989	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7640	Approved
0.6981	Remote Similarity	NPD7639	Approved
0.6961	Remote Similarity	NPD7637	Suspended
0.6961	Remote Similarity	NPD6411	Approved
0.6957	Remote Similarity	NPD6009	Approved
0.6952	Remote Similarity	NPD6083	Phase 2
0.6952	Remote Similarity	NPD6084	Phase 2
0.6947	Remote Similarity	NPD7645	Phase 2
0.6939	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4786	Approved
0.6923	Remote Similarity	NPD6059	Approved
0.6907	Remote Similarity	NPD3667	Approved
0.6903	Remote Similarity	NPD8297	Approved
0.6891	Remote Similarity	NPD6067	Discontinued
0.6885	Remote Similarity	NPD7319	Approved
0.6875	Remote Similarity	NPD7525	Registered
0.6864	Remote Similarity	NPD8517	Approved
0.6864	Remote Similarity	NPD6016	Approved
0.6864	Remote Similarity	NPD6015	Approved
0.6864	Remote Similarity	NPD8516	Approved
0.6864	Remote Similarity	NPD8513	Phase 3
0.6864	Remote Similarity	NPD8515	Approved
0.6847	Remote Similarity	NPD6899	Approved
0.6847	Remote Similarity	NPD6881	Approved
0.6842	Remote Similarity	NPD4632	Approved
0.6837	Remote Similarity	NPD6695	Phase 3
0.6827	Remote Similarity	NPD7748	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6814	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7115	Discovery
0.6809	Remote Similarity	NPD6933	Approved
0.6807	Remote Similarity	NPD5988	Approved
0.68	Remote Similarity	NPD7334	Approved
0.68	Remote Similarity	NPD7521	Approved
0.68	Remote Similarity	NPD6684	Approved
0.68	Remote Similarity	NPD5330	Approved
0.68	Remote Similarity	NPD7146	Approved
0.68	Remote Similarity	NPD6409	Approved
0.6796	Remote Similarity	NPD7515	Phase 2
0.6792	Remote Similarity	NPD7902	Approved
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6319	Approved
0.6765	Remote Similarity	NPD6101	Approved
0.6765	Remote Similarity	NPD6051	Approved
0.6765	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5344	Discontinued
0.6757	Remote Similarity	NPD5697	Approved
0.6726	Remote Similarity	NPD7102	Approved
0.6726	Remote Similarity	NPD7290	Approved
0.6726	Remote Similarity	NPD6883	Approved
0.6699	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6637	Remote Similarity	NPD6013	Approved
0.6637	Remote Similarity	NPD6014	Approved
0.6637	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD6373	Approved
0.6637	Remote Similarity	NPD6372	Approved
0.6607	Remote Similarity	NPD5701	Approved
0.6604	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD3666	Approved
0.66	Remote Similarity	NPD3665	Phase 1
0.66	Remote Similarity	NPD3133	Approved
0.6598	Remote Similarity	NPD6929	Approved
0.6596	Remote Similarity	NPD4784	Approved
0.6596	Remote Similarity	NPD6926	Approved
0.6596	Remote Similarity	NPD4785	Approved
0.6596	Remote Similarity	NPD6924	Approved
0.6587	Remote Similarity	NPD8449	Approved
0.6574	Remote Similarity	NPD5696	Approved
0.6574	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5779	Approved
0.6571	Remote Similarity	NPD8171	Discontinued
0.6571	Remote Similarity	NPD5778	Approved
0.6569	Remote Similarity	NPD7750	Discontinued
0.6562	Remote Similarity	NPD6932	Approved
0.6549	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6011	Approved
0.6538	Remote Similarity	NPD46	Approved
0.6538	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD8450	Suspended
0.6531	Remote Similarity	NPD6930	Phase 2
0.6531	Remote Similarity	NPD6931	Approved
0.6518	Remote Similarity	NPD6008	Approved
0.6509	Remote Similarity	NPD7900	Approved
0.6509	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7145	Approved
0.6476	Remote Similarity	NPD6079	Approved
0.6476	Remote Similarity	NPD8035	Phase 2
0.6476	Remote Similarity	NPD8034	Phase 2
0.6476	Remote Similarity	NPD7983	Approved
0.6475	Remote Similarity	NPD7604	Phase 2
0.6471	Remote Similarity	NPD3618	Phase 1
0.6452	Remote Similarity	NPD7143	Approved
0.6452	Remote Similarity	NPD7144	Approved
0.6446	Remote Similarity	NPD5983	Phase 2
0.6442	Remote Similarity	NPD5328	Approved
0.6442	Remote Similarity	NPD4753	Phase 2
0.6436	Remote Similarity	NPD3668	Phase 3
0.6435	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4195	Approved
0.6429	Remote Similarity	NPD5956	Approved
0.6408	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4250	Approved
0.6408	Remote Similarity	NPD4251	Approved
0.64	Remote Similarity	NPD6033	Approved
0.6396	Remote Similarity	NPD7632	Discontinued
0.6392	Remote Similarity	NPD5776	Phase 2
0.6392	Remote Similarity	NPD6925	Approved
0.6383	Remote Similarity	NPD4243	Approved
0.6383	Remote Similarity	NPD7151	Approved
0.6383	Remote Similarity	NPD7150	Approved
0.6383	Remote Similarity	NPD7152	Approved
0.6379	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6336	Discontinued
0.6364	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD7332	Phase 2
0.6364	Remote Similarity	NPD7509	Discontinued
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD7514	Phase 3
0.6364	Remote Similarity	NPD5285	Approved
0.6364	Remote Similarity	NPD6648	Approved
0.6344	Remote Similarity	NPD6923	Approved
0.6344	Remote Similarity	NPD6922	Approved
0.633	Remote Similarity	NPD4755	Approved
0.6325	Remote Similarity	NPD6053	Discontinued
0.6321	Remote Similarity	NPD7087	Discontinued
0.6321	Remote Similarity	NPD5284	Approved
0.6321	Remote Similarity	NPD5281	Approved
0.632	Remote Similarity	NPD8074	Phase 3
0.6311	Remote Similarity	NPD4249	Approved
0.6311	Remote Similarity	NPD6098	Approved
0.63	Remote Similarity	NPD6902	Approved
0.6296	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4629	Approved
0.6293	Remote Similarity	NPD4634	Approved
0.6286	Remote Similarity	NPD6080	Approved
0.6286	Remote Similarity	NPD6673	Approved
0.6286	Remote Similarity	NPD6904	Approved
0.6286	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7101	Approved
0.6281	Remote Similarity	NPD7100	Approved
0.6263	Remote Similarity	NPD6683	Phase 2
0.6262	Remote Similarity	NPD4202	Approved
0.626	Remote Similarity	NPD5126	Approved
0.626	Remote Similarity	NPD5125	Phase 3
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD5211	Phase 2

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