NPASS Compound

Structure

NPC159876 OpenBabel07101718312D 30 33 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 -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 -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 -1.3766 2.1910 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 -1.1924 -1.3243 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 5 2 0 0 0 0 5 23 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 26 1 0 0 0 0 15 24 1 0 0 0 0 15 29 1 0 0 0 0 16 25 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 6 0 0 0 19 14 1 6 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 21 22 1 0 0 0 0 21 28 1 6 0 0 0 22 29 1 1 0 0 0 22 30 1 0 0 0 0 23 2 1 1 0 0 0 24 3 1 6 0 0 0 25 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.29
Volume:	445.408
LogP:	4.748
LogD:	3.578
LogS:	-4.389
# Rotatable Bonds:	5
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	5.1
Fsp3:	0.84
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:	-5.076
MDCK Permeability:	4.788895694218809e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.075
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.792
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	84.83597564697266%
Volume Distribution (VD):	1.425
Pgp-substrate:	13.978994369506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.724
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	2.293
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.598
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.348
Carcinogencity:	0.235
Eye Corrosion:	0.004
Eye Irritation:	0.03
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC159876

Natural Product ID:	NPC159876
*Common Name:**	Sagittine B
IUPAC Name:	(2R,3R,4R,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]-5-(hydroxymethyl)oxolane-3,4-diol
Synonyms:	sagittine B
Standard InCHIKey:	VNFVCQOGUQDMEA-RGIBMUORSA-N
Standard InCHI:	InChI=1S/C25H40O5/c1-5-23(2)11-12-25(4)16(13-23)8-9-17-18(25)7-6-10-24(17,3)15-29-22-21(28)20(27)19(14-26)30-22/h5,9,16,18-22,26-28H,1,6-8,10-15H2,2-4H3/t16-,18-,19-,20-,21+,22+,23-,24+,25-/m0/s1
SMILES:	OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)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:	CHEMBL482046
PubChem CID:	11647447
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[528170]
NPT4399	Organism	Actinomyces naeslundii	Actinomyces naeslundii	MIC	=	125.0	ug.mL-1	PMID[528170]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	62.5	ug.mL-1	PMID[528170]

☑ 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 NPC159876 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	181
0.1-0.2	1231
0.2-0.3	5070
0.3-0.4	13628
0.4-0.5	9062
0.5-0.6	6165
0.6-0.7	5460
0.7-0.8	1744
0.8-0.85	122
0.85-0.9	27
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC473058
0.9545	High Similarity	NPC286612
0.9545	High Similarity	NPC230347
0.9545	High Similarity	NPC275310
0.9222	High Similarity	NPC207617
0.9022	High Similarity	NPC158088
0.9	High Similarity	NPC305160
0.8913	High Similarity	NPC473890
0.8913	High Similarity	NPC243728
0.8889	High Similarity	NPC91654
0.8889	High Similarity	NPC67398
0.8889	High Similarity	NPC474792
0.8837	High Similarity	NPC319238
0.883	High Similarity	NPC21064
0.883	High Similarity	NPC121072
0.883	High Similarity	NPC267510
0.8817	High Similarity	NPC216260
0.8817	High Similarity	NPC5358
0.8791	High Similarity	NPC477927
0.8791	High Similarity	NPC72817
0.8778	High Similarity	NPC302584
0.8737	High Similarity	NPC272015
0.8737	High Similarity	NPC154452
0.8723	High Similarity	NPC282669
0.8723	High Similarity	NPC469942
0.8632	High Similarity	NPC285231
0.8632	High Similarity	NPC21568
0.8632	High Similarity	NPC470434
0.8621	High Similarity	NPC166279
0.8587	High Similarity	NPC211238
0.8526	High Similarity	NPC324598
0.8526	High Similarity	NPC473790
0.8511	High Similarity	NPC309503
0.8511	High Similarity	NPC240372
0.8511	High Similarity	NPC125551
0.8511	High Similarity	NPC91197
0.8511	High Similarity	NPC239547
0.8511	High Similarity	NPC155319
0.8511	High Similarity	NPC96597
0.8469	Intermediate Similarity	NPC181845
0.8454	Intermediate Similarity	NPC99627
0.8454	Intermediate Similarity	NPC473129
0.8427	Intermediate Similarity	NPC470836
0.8421	Intermediate Similarity	NPC234287
0.8421	Intermediate Similarity	NPC280825
0.8421	Intermediate Similarity	NPC309493
0.8421	Intermediate Similarity	NPC477928
0.8404	Intermediate Similarity	NPC90583
0.8384	Intermediate Similarity	NPC283829
0.8384	Intermediate Similarity	NPC470432
0.8384	Intermediate Similarity	NPC14704
0.8384	Intermediate Similarity	NPC226642
0.8384	Intermediate Similarity	NPC305423
0.8384	Intermediate Similarity	NPC230507
0.8384	Intermediate Similarity	NPC113044
0.8384	Intermediate Similarity	NPC161676
0.8384	Intermediate Similarity	NPC33053
0.837	Intermediate Similarity	NPC48463
0.8367	Intermediate Similarity	NPC109792
0.8367	Intermediate Similarity	NPC31430
0.8367	Intermediate Similarity	NPC121566
0.8367	Intermediate Similarity	NPC85593
0.8367	Intermediate Similarity	NPC75608
0.8367	Intermediate Similarity	NPC221562
0.8367	Intermediate Similarity	NPC54521
0.8367	Intermediate Similarity	NPC187400
0.8367	Intermediate Similarity	NPC57065
0.8367	Intermediate Similarity	NPC100955
0.8367	Intermediate Similarity	NPC93352
0.8367	Intermediate Similarity	NPC470885
0.8352	Intermediate Similarity	NPC477917
0.8352	Intermediate Similarity	NPC470819
0.8351	Intermediate Similarity	NPC136816
0.8333	Intermediate Similarity	NPC473200
0.8333	Intermediate Similarity	NPC64348
0.8333	Intermediate Similarity	NPC7341
0.83	Intermediate Similarity	NPC476538
0.83	Intermediate Similarity	NPC476539
0.83	Intermediate Similarity	NPC476540
0.83	Intermediate Similarity	NPC98696
0.83	Intermediate Similarity	NPC476541
0.8298	Intermediate Similarity	NPC477969
0.8298	Intermediate Similarity	NPC135224
0.8298	Intermediate Similarity	NPC100892
0.8298	Intermediate Similarity	NPC477970
0.8283	Intermediate Similarity	NPC474569
0.8283	Intermediate Similarity	NPC309448
0.8283	Intermediate Similarity	NPC473923
0.8283	Intermediate Similarity	NPC95243
0.8283	Intermediate Similarity	NPC242748
0.8283	Intermediate Similarity	NPC63023
0.8283	Intermediate Similarity	NPC473476
0.8283	Intermediate Similarity	NPC26798
0.8265	Intermediate Similarity	NPC475701
0.8265	Intermediate Similarity	NPC473198
0.8265	Intermediate Similarity	NPC213190
0.8261	Intermediate Similarity	NPC470817
0.8247	Intermediate Similarity	NPC117714
0.8247	Intermediate Similarity	NPC472023
0.8247	Intermediate Similarity	NPC88000
0.8247	Intermediate Similarity	NPC4831
0.8247	Intermediate Similarity	NPC47566
0.8247	Intermediate Similarity	NPC160734
0.8247	Intermediate Similarity	NPC129372
0.8247	Intermediate Similarity	NPC263756
0.8247	Intermediate Similarity	NPC309425
0.8242	Intermediate Similarity	NPC319030
0.8222	Intermediate Similarity	NPC173917
0.8218	Intermediate Similarity	NPC475333
0.8218	Intermediate Similarity	NPC232054
0.8218	Intermediate Similarity	NPC40440
0.8218	Intermediate Similarity	NPC194207
0.8218	Intermediate Similarity	NPC208383
0.8218	Intermediate Similarity	NPC477809
0.8218	Intermediate Similarity	NPC42482
0.8218	Intermediate Similarity	NPC84956
0.8218	Intermediate Similarity	NPC102016
0.8218	Intermediate Similarity	NPC150372
0.8218	Intermediate Similarity	NPC244086
0.8218	Intermediate Similarity	NPC475670
0.8218	Intermediate Similarity	NPC477027
0.8218	Intermediate Similarity	NPC470433
0.8218	Intermediate Similarity	NPC248746
0.8218	Intermediate Similarity	NPC475550
0.8218	Intermediate Similarity	NPC224098
0.8218	Intermediate Similarity	NPC70204
0.8218	Intermediate Similarity	NPC73243
0.8218	Intermediate Similarity	NPC95051
0.8218	Intermediate Similarity	NPC171073
0.8218	Intermediate Similarity	NPC300557
0.8218	Intermediate Similarity	NPC249265
0.8218	Intermediate Similarity	NPC477026
0.8218	Intermediate Similarity	NPC218571
0.8218	Intermediate Similarity	NPC46190
0.8218	Intermediate Similarity	NPC6806
0.8218	Intermediate Similarity	NPC22779
0.8218	Intermediate Similarity	NPC306131
0.8218	Intermediate Similarity	NPC309278
0.82	Intermediate Similarity	NPC257964
0.82	Intermediate Similarity	NPC94272
0.82	Intermediate Similarity	NPC190395
0.82	Intermediate Similarity	NPC293512
0.8191	Intermediate Similarity	NPC189513
0.8191	Intermediate Similarity	NPC96736
0.8191	Intermediate Similarity	NPC178949
0.8182	Intermediate Similarity	NPC474464
0.8182	Intermediate Similarity	NPC470043
0.8182	Intermediate Similarity	NPC475365
0.8182	Intermediate Similarity	NPC470061
0.8182	Intermediate Similarity	NPC470062
0.8182	Intermediate Similarity	NPC470058
0.8182	Intermediate Similarity	NPC470059
0.8182	Intermediate Similarity	NPC470060
0.8182	Intermediate Similarity	NPC470057
0.8182	Intermediate Similarity	NPC470064
0.8163	Intermediate Similarity	NPC159036
0.8163	Intermediate Similarity	NPC256133
0.8163	Intermediate Similarity	NPC76497
0.8163	Intermediate Similarity	NPC30289
0.8163	Intermediate Similarity	NPC288694
0.8163	Intermediate Similarity	NPC213674
0.8163	Intermediate Similarity	NPC470571
0.8163	Intermediate Similarity	NPC312553
0.8161	Intermediate Similarity	NPC100697
0.8152	Intermediate Similarity	NPC309310
0.8137	Intermediate Similarity	NPC247037
0.8137	Intermediate Similarity	NPC103627
0.8137	Intermediate Similarity	NPC87998
0.8137	Intermediate Similarity	NPC224314
0.8137	Intermediate Similarity	NPC191439
0.8137	Intermediate Similarity	NPC23808
0.8137	Intermediate Similarity	NPC141433
0.8137	Intermediate Similarity	NPC222202
0.8137	Intermediate Similarity	NPC477811
0.8137	Intermediate Similarity	NPC170974
0.8137	Intermediate Similarity	NPC269297
0.8125	Intermediate Similarity	NPC177818
0.8125	Intermediate Similarity	NPC98112
0.8119	Intermediate Similarity	NPC128795
0.8119	Intermediate Similarity	NPC217921
0.8119	Intermediate Similarity	NPC295980
0.8119	Intermediate Similarity	NPC126147
0.8119	Intermediate Similarity	NPC135015
0.8119	Intermediate Similarity	NPC38376
0.8119	Intermediate Similarity	NPC295389
0.8119	Intermediate Similarity	NPC80210
0.8119	Intermediate Similarity	NPC48548
0.8111	Intermediate Similarity	NPC119001
0.81	Intermediate Similarity	NPC474015
0.81	Intermediate Similarity	NPC470767
0.81	Intermediate Similarity	NPC470056
0.81	Intermediate Similarity	NPC472899
0.81	Intermediate Similarity	NPC472900
0.81	Intermediate Similarity	NPC470055
0.81	Intermediate Similarity	NPC472898
0.81	Intermediate Similarity	NPC470763
0.8085	Intermediate Similarity	NPC242419
0.8085	Intermediate Similarity	NPC474835
0.8085	Intermediate Similarity	NPC235126
0.8081	Intermediate Similarity	NPC471888

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 NPC159876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1434
0.2-0.3	4231
0.3-0.4	2238
0.4-0.5	604
0.5-0.6	241
0.6-0.7	211
0.7-0.8	29
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
0.802	Intermediate Similarity	NPD6412	Phase 2
0.7596	Intermediate Similarity	NPD6686	Approved
0.7386	Intermediate Similarity	NPD7339	Approved
0.7386	Intermediate Similarity	NPD6942	Approved
0.7368	Intermediate Similarity	NPD7524	Approved
0.7303	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7503	Approved
0.7253	Intermediate Similarity	NPD7645	Phase 2
0.7234	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6370	Approved
0.7174	Intermediate Similarity	NPD7525	Registered
0.7143	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD7328	Approved
0.7128	Intermediate Similarity	NPD6695	Phase 3
0.7111	Intermediate Similarity	NPD6933	Approved
0.7105	Intermediate Similarity	NPD8033	Approved
0.708	Intermediate Similarity	NPD7516	Approved
0.7018	Intermediate Similarity	NPD6054	Approved
0.7018	Intermediate Similarity	NPD8294	Approved
0.7018	Intermediate Similarity	NPD8377	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6957	Remote Similarity	NPD8296	Approved
0.6957	Remote Similarity	NPD8335	Approved
0.6957	Remote Similarity	NPD8378	Approved
0.6957	Remote Similarity	NPD8380	Approved
0.6957	Remote Similarity	NPD8379	Approved
0.6903	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7736	Approved
0.6889	Remote Similarity	NPD4784	Approved
0.6889	Remote Similarity	NPD6924	Approved
0.6889	Remote Similarity	NPD4785	Approved
0.6889	Remote Similarity	NPD6926	Approved
0.6882	Remote Similarity	NPD6929	Approved
0.6875	Remote Similarity	NPD4786	Approved
0.687	Remote Similarity	NPD6059	Approved
0.6848	Remote Similarity	NPD6932	Approved
0.6842	Remote Similarity	NPD3667	Approved
0.6838	Remote Similarity	NPD6067	Discontinued
0.6838	Remote Similarity	NPD8328	Phase 3
0.6837	Remote Similarity	NPD7750	Discontinued
0.6832	Remote Similarity	NPD8171	Discontinued
0.6827	Remote Similarity	NPD4225	Approved
0.681	Remote Similarity	NPD6015	Approved
0.681	Remote Similarity	NPD6016	Approved
0.6809	Remote Similarity	NPD6931	Approved
0.6809	Remote Similarity	NPD6930	Phase 2
0.6807	Remote Similarity	NPD8293	Discontinued
0.6803	Remote Similarity	NPD8449	Approved
0.6786	Remote Similarity	NPD8133	Approved
0.678	Remote Similarity	NPD7492	Approved
0.6774	Remote Similarity	NPD7145	Approved
0.6752	Remote Similarity	NPD5988	Approved
0.6748	Remote Similarity	NPD8450	Suspended
0.6742	Remote Similarity	NPD7143	Approved
0.6742	Remote Similarity	NPD7144	Approved
0.6723	Remote Similarity	NPD7507	Approved
0.6723	Remote Similarity	NPD6616	Approved
0.6701	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6632	Remote Similarity	NPD7332	Phase 2
0.6632	Remote Similarity	NPD7509	Discontinued
0.6632	Remote Similarity	NPD7514	Phase 3
0.6629	Remote Similarity	NPD6923	Approved
0.6629	Remote Similarity	NPD6922	Approved
0.6609	Remote Similarity	NPD6009	Approved
0.6604	Remote Similarity	NPD7640	Approved
0.6604	Remote Similarity	NPD7639	Approved
0.6571	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD6084	Phase 2
0.6569	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD7087	Discontinued
0.6569	Remote Similarity	NPD6411	Approved
0.6562	Remote Similarity	NPD6902	Approved
0.6557	Remote Similarity	NPD7319	Approved
0.6549	Remote Similarity	NPD8297	Approved
0.6531	Remote Similarity	NPD3665	Phase 1
0.6531	Remote Similarity	NPD3666	Approved
0.6531	Remote Similarity	NPD3133	Approved
0.6526	Remote Similarity	NPD6683	Phase 2
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.6525	Remote Similarity	NPD8515	Approved
0.6491	Remote Similarity	NPD4632	Approved
0.6486	Remote Similarity	NPD6899	Approved
0.6486	Remote Similarity	NPD6881	Approved
0.6471	Remote Similarity	NPD5125	Phase 3
0.6471	Remote Similarity	NPD3168	Discontinued
0.6471	Remote Similarity	NPD5126	Approved
0.6466	Remote Similarity	NPD7115	Discovery
0.6465	Remote Similarity	NPD6893	Approved
0.646	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6928	Phase 2
0.6455	Remote Similarity	NPD6675	Approved
0.6455	Remote Similarity	NPD6402	Approved
0.6455	Remote Similarity	NPD7128	Approved
0.6455	Remote Similarity	NPD5739	Approved
0.6452	Remote Similarity	NPD8264	Approved
0.6442	Remote Similarity	NPD7748	Approved
0.6441	Remote Similarity	NPD6319	Approved
0.6429	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7902	Approved
0.6408	Remote Similarity	NPD6079	Approved
0.6408	Remote Similarity	NPD7515	Phase 2
0.64	Remote Similarity	NPD7146	Approved
0.64	Remote Similarity	NPD3618	Phase 1
0.64	Remote Similarity	NPD6409	Approved
0.64	Remote Similarity	NPD7334	Approved
0.64	Remote Similarity	NPD7521	Approved
0.64	Remote Similarity	NPD6684	Approved
0.64	Remote Similarity	NPD5330	Approved
0.6396	Remote Similarity	NPD5697	Approved
0.6392	Remote Similarity	NPD6898	Phase 1
0.6389	Remote Similarity	NPD5344	Discontinued
0.6373	Remote Similarity	NPD5328	Approved
0.6373	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4753	Phase 2
0.6373	Remote Similarity	NPD6101	Approved
0.6373	Remote Similarity	NPD6051	Approved
0.6372	Remote Similarity	NPD7290	Approved
0.6372	Remote Similarity	NPD7102	Approved
0.6372	Remote Similarity	NPD6883	Approved
0.6371	Remote Similarity	NPD5956	Approved
0.6364	Remote Similarity	NPD3668	Phase 3
0.6354	Remote Similarity	NPD4195	Approved
0.6344	Remote Similarity	NPD1811	Approved
0.6344	Remote Similarity	NPD1810	Approved
0.6341	Remote Similarity	NPD6033	Approved
0.6339	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD6617	Approved
0.6316	Remote Similarity	NPD8130	Phase 1
0.6316	Remote Similarity	NPD6869	Approved
0.6316	Remote Similarity	NPD6847	Approved
0.6316	Remote Similarity	NPD6649	Approved
0.6316	Remote Similarity	NPD6650	Approved
0.6311	Remote Similarity	NPD7838	Discovery
0.6296	Remote Similarity	NPD5285	Approved
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.6289	Remote Similarity	NPD4748	Discontinued
0.6283	Remote Similarity	NPD6373	Approved
0.6283	Remote Similarity	NPD6014	Approved
0.6283	Remote Similarity	NPD6372	Approved
0.6283	Remote Similarity	NPD6013	Approved
0.6283	Remote Similarity	NPD6012	Approved
0.6279	Remote Similarity	NPD1145	Discontinued
0.6277	Remote Similarity	NPD4190	Phase 3
0.6277	Remote Similarity	NPD5275	Approved
0.6275	Remote Similarity	NPD6672	Approved
0.6275	Remote Similarity	NPD5737	Approved
0.6275	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6903	Approved
0.6262	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD4159	Approved
0.6228	Remote Similarity	NPD4634	Approved
0.6226	Remote Similarity	NPD4629	Approved
0.6226	Remote Similarity	NPD5210	Approved
0.6226	Remote Similarity	NPD5695	Phase 3
0.6216	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5696	Approved
0.6204	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6011	Approved
0.6195	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4202	Approved
0.619	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD5778	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.6182	Remote Similarity	NPD5211	Phase 2
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.6168	Remote Similarity	NPD5221	Approved
0.6168	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5222	Approved
0.6161	Remote Similarity	NPD6008	Approved
0.6161	Remote Similarity	NPD6640	Phase 3
0.6154	Remote Similarity	NPD6698	Approved
0.6154	Remote Similarity	NPD46	Approved
0.6154	Remote Similarity	NPD7136	Phase 2
0.6148	Remote Similarity	NPD7604	Phase 2
0.6147	Remote Similarity	NPD4700	Approved
0.6132	Remote Similarity	NPD5282	Discontinued
0.6132	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7900	Approved
0.6126	Remote Similarity	NPD5174	Approved
0.6126	Remote Similarity	NPD5175	Approved
0.6122	Remote Similarity	NPD4695	Discontinued
0.6116	Remote Similarity	NPD5983	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