NPASS Compound

Structure

NPC216260 OpenBabel07101719132D 36 40 0 0 1 0 0 0 0 0999 V2000 4.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8023 2.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2091 1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 -2.6844 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 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 -3.3305 0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 1 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 0 0 0 0 0 0 0 0 0 0 -4.1965 0.1303 0.0000 C 0 0 2 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 3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1100 0.5371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9941 -0.9523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2146 1.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9191 -0.0507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4055 2.1194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4941 -1.8184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9886 -0.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 35 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 18 17 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 31 1 0 0 0 0 22 25 1 1 0 0 0 22 36 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 1 0 0 0 24 27 1 0 0 0 0 24 32 1 1 0 0 0 25 28 1 0 0 0 0 25 33 1 6 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 28 34 1 0 0 0 0 29 5 1 1 0 0 0 30 31 1 6 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.38
Volume:	543.264
LogP:	5.537
LogD:	4.643
LogS:	-4.228
# Rotatable Bonds:	4
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	5.139
Fsp3:	0.935
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.742
MDCK Permeability:	1.1673770131892525e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.552

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	93.22078704833984%
Volume Distribution (VD):	1.826
Pgp-substrate:	4.80435037612915%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.306
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.843
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.534
CYP3A4-substrate:	0.544

ADMET: Excretion

Clearance (CL):	7.785
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.236
Carcinogencity:	0.063
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC216260

Natural Product ID:	NPC216260
*Common Name:**	Agladupol D
IUPAC Name:	(1S)-1-[(2R,4S,5R)-4-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-methoxyoxolan-2-yl]-2-methylpropane-1,2-diol
Synonyms:
Standard InCHIKey:	PNEVHPUMSSFAQE-FECCMMPESA-N
Standard InCHI:	InChI=1S/C31H52O5/c1-27(2)23-10-9-21-20(29(23,5)14-13-24(27)32)12-16-30(6)19(11-15-31(21,30)7)18-17-22(36-26(18)35-8)25(33)28(3,4)34/h9,18-20,22-26,32-34H,10-17H2,1-8H3/t18-,19-,20-,22+,23-,24-,25-,26+,29+,30-,31+/m0/s1
SMILES:	CC1(C)[C@@H]2CC=C3[C@H](CC[C@@]4(C)[C@@H](CC[C@]34C)[C@@H]3C[C@H]([C@@H](C(C)(C)O)O)O[C@H]3OC)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2392320
PubChem CID:	73354987
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO3063	Aphanamixis grandifolia	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23772699]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3063	Aphanamixis grandifolia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18932	Melia azedarach	Species	Meliaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	670.0	nM	PMID[480570]

☑ 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 NPC216260 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	218
0.1-0.2	1640
0.2-0.3	5814
0.3-0.4	13619
0.4-0.5	8666
0.5-0.6	5436
0.6-0.7	4797
0.7-0.8	2107
0.8-0.85	304
0.85-0.9	81
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC5358
0.9677	High Similarity	NPC324598
0.9479	High Similarity	NPC85593
0.9479	High Similarity	NPC31430
0.9375	High Similarity	NPC213190
0.9184	High Similarity	NPC26798
0.9175	High Similarity	NPC475701
0.9167	High Similarity	NPC160734
0.9167	High Similarity	NPC309425
0.9167	High Similarity	NPC129372
0.9167	High Similarity	NPC88000
0.9167	High Similarity	NPC4831
0.9167	High Similarity	NPC472023
0.9167	High Similarity	NPC47566
0.9158	High Similarity	NPC280825
0.9158	High Similarity	NPC234287
0.9091	High Similarity	NPC226642
0.9082	High Similarity	NPC221562
0.9082	High Similarity	NPC187400
0.9082	High Similarity	NPC470885
0.9082	High Similarity	NPC474464
0.9072	High Similarity	NPC136816
0.9062	High Similarity	NPC473200
0.9062	High Similarity	NPC7341
0.9053	High Similarity	NPC473890
0.9053	High Similarity	NPC243728
0.901	High Similarity	NPC191439
0.901	High Similarity	NPC103627
0.901	High Similarity	NPC170974
0.901	High Similarity	NPC101450
0.9	High Similarity	NPC220427
0.899	High Similarity	NPC474015
0.898	High Similarity	NPC155010
0.898	High Similarity	NPC16520
0.898	High Similarity	NPC471885
0.898	High Similarity	NPC286969
0.898	High Similarity	NPC471886
0.898	High Similarity	NPC114874
0.898	High Similarity	NPC131479
0.898	High Similarity	NPC472252
0.898	High Similarity	NPC120123
0.898	High Similarity	NPC189852
0.898	High Similarity	NPC473020
0.898	High Similarity	NPC471887
0.898	High Similarity	NPC157659
0.898	High Similarity	NPC211879
0.898	High Similarity	NPC471888
0.898	High Similarity	NPC31907
0.898	High Similarity	NPC8039
0.898	High Similarity	NPC245280
0.8958	High Similarity	NPC158088
0.8958	High Similarity	NPC309493
0.8947	High Similarity	NPC207617
0.8936	High Similarity	NPC305160
0.8925	High Similarity	NPC210268
0.8922	High Similarity	NPC208189
0.8922	High Similarity	NPC65034
0.8922	High Similarity	NPC197231
0.8913	High Similarity	NPC473058
0.8911	High Similarity	NPC473318
0.8911	High Similarity	NPC250089
0.8911	High Similarity	NPC476835
0.8911	High Similarity	NPC28844
0.8911	High Similarity	NPC14630
0.8911	High Similarity	NPC157530
0.8911	High Similarity	NPC473328
0.89	High Similarity	NPC190395
0.8889	High Similarity	NPC121566
0.8889	High Similarity	NPC470064
0.8889	High Similarity	NPC470061
0.8889	High Similarity	NPC470059
0.8889	High Similarity	NPC470062
0.8889	High Similarity	NPC165033
0.8889	High Similarity	NPC470057
0.8889	High Similarity	NPC470060
0.8889	High Similarity	NPC470058
0.8889	High Similarity	NPC470043
0.8889	High Similarity	NPC475365
0.8889	High Similarity	NPC75608
0.8889	High Similarity	NPC273879
0.8889	High Similarity	NPC471111
0.8889	High Similarity	NPC100955
0.8878	High Similarity	NPC22634
0.8878	High Similarity	NPC288694
0.8878	High Similarity	NPC471482
0.8878	High Similarity	NPC312553
0.8878	High Similarity	NPC159036
0.8878	High Similarity	NPC300399
0.8878	High Similarity	NPC37207
0.8866	High Similarity	NPC282669
0.8835	High Similarity	NPC19888
0.8835	High Similarity	NPC231797
0.883	High Similarity	NPC98193
0.8824	High Similarity	NPC65155
0.8817	High Similarity	NPC159876
0.8812	High Similarity	NPC476538
0.8812	High Similarity	NPC476539
0.8812	High Similarity	NPC476540
0.8812	High Similarity	NPC476541
0.88	High Similarity	NPC242748
0.88	High Similarity	NPC309448
0.88	High Similarity	NPC208477
0.88	High Similarity	NPC160816
0.88	High Similarity	NPC473199
0.88	High Similarity	NPC63023
0.88	High Similarity	NPC269627
0.88	High Similarity	NPC152584
0.88	High Similarity	NPC95243
0.88	High Similarity	NPC472900
0.88	High Similarity	NPC69737
0.88	High Similarity	NPC127801
0.88	High Similarity	NPC472898
0.88	High Similarity	NPC194842
0.88	High Similarity	NPC472899
0.88	High Similarity	NPC208594
0.88	High Similarity	NPC181845
0.8788	High Similarity	NPC473198
0.8788	High Similarity	NPC16573
0.8788	High Similarity	NPC471450
0.8776	High Similarity	NPC474022
0.8776	High Similarity	NPC267510
0.8776	High Similarity	NPC470434
0.8763	High Similarity	NPC275865
0.875	High Similarity	NPC472989
0.875	High Similarity	NPC90583
0.875	High Similarity	NPC476671
0.8737	High Similarity	NPC72817
0.8737	High Similarity	NPC477927
0.8725	High Similarity	NPC477026
0.8725	High Similarity	NPC477027
0.8725	High Similarity	NPC128133
0.8725	High Similarity	NPC70204
0.8725	High Similarity	NPC475670
0.8725	High Similarity	NPC42482
0.8725	High Similarity	NPC302057
0.8725	High Similarity	NPC306131
0.8725	High Similarity	NPC40440
0.8713	High Similarity	NPC231340
0.8713	High Similarity	NPC305423
0.8713	High Similarity	NPC181467
0.8713	High Similarity	NPC470432
0.8713	High Similarity	NPC230507
0.8713	High Similarity	NPC161676
0.8713	High Similarity	NPC113044
0.8713	High Similarity	NPC63368
0.8713	High Similarity	NPC14704
0.8713	High Similarity	NPC283829
0.8713	High Similarity	NPC33053
0.8713	High Similarity	NPC208650
0.8713	High Similarity	NPC14946
0.87	High Similarity	NPC93352
0.8687	High Similarity	NPC154452
0.8687	High Similarity	NPC272015
0.8687	High Similarity	NPC471889
0.8673	High Similarity	NPC469942
0.8667	High Similarity	NPC477810
0.866	High Similarity	NPC177818
0.8627	High Similarity	NPC246124
0.8627	High Similarity	NPC98696
0.8627	High Similarity	NPC38217
0.8627	High Similarity	NPC159005
0.8627	High Similarity	NPC472988
0.8627	High Similarity	NPC6931
0.8627	High Similarity	NPC180183
0.8614	High Similarity	NPC470056
0.8614	High Similarity	NPC470055
0.8614	High Similarity	NPC474569
0.8614	High Similarity	NPC473923
0.8614	High Similarity	NPC473476
0.8586	High Similarity	NPC285231
0.8586	High Similarity	NPC21064
0.8586	High Similarity	NPC21568
0.8586	High Similarity	NPC121072
0.8571	High Similarity	NPC476693
0.8571	High Similarity	NPC144068
0.8571	High Similarity	NPC476895
0.8558	High Similarity	NPC13190
0.8558	High Similarity	NPC477032
0.8558	High Similarity	NPC475247
0.8558	High Similarity	NPC477028
0.8558	High Similarity	NPC294129
0.8558	High Similarity	NPC476547
0.8558	High Similarity	NPC124677
0.8544	High Similarity	NPC470433
0.8544	High Similarity	NPC472901
0.8544	High Similarity	NPC249265
0.8544	High Similarity	NPC248746
0.8544	High Similarity	NPC477809
0.8544	High Similarity	NPC475550
0.8544	High Similarity	NPC208383
0.8544	High Similarity	NPC46190
0.8544	High Similarity	NPC22779
0.8544	High Similarity	NPC232054
0.8544	High Similarity	NPC43976
0.8544	High Similarity	NPC6806
0.8544	High Similarity	NPC296761
0.8544	High Similarity	NPC224098
0.8544	High Similarity	NPC171073
0.8544	High Similarity	NPC73243
0.8544	High Similarity	NPC309278

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 NPC216260 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1900
0.2-0.3	4328
0.3-0.4	1832
0.4-0.5	454
0.5-0.6	213
0.6-0.7	194
0.7-0.8	47
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
0.8091	Intermediate Similarity	NPD7328	Approved
0.8091	Intermediate Similarity	NPD7327	Approved
0.8018	Intermediate Similarity	NPD7516	Approved
0.8	Intermediate Similarity	NPD6412	Phase 2
0.7965	Intermediate Similarity	NPD6370	Approved
0.7946	Intermediate Similarity	NPD8377	Approved
0.7946	Intermediate Similarity	NPD8294	Approved
0.7935	Intermediate Similarity	NPD7525	Registered
0.7876	Intermediate Similarity	NPD8380	Approved
0.7876	Intermediate Similarity	NPD8379	Approved
0.7876	Intermediate Similarity	NPD8378	Approved
0.7876	Intermediate Similarity	NPD8296	Approved
0.7876	Intermediate Similarity	NPD8033	Approved
0.7876	Intermediate Similarity	NPD8335	Approved
0.7788	Intermediate Similarity	NPD6054	Approved
0.7788	Intermediate Similarity	NPD6059	Approved
0.7719	Intermediate Similarity	NPD7503	Approved
0.7692	Intermediate Similarity	NPD8293	Discontinued
0.7627	Intermediate Similarity	NPD7736	Approved
0.7607	Intermediate Similarity	NPD7507	Approved
0.7565	Intermediate Similarity	NPD6015	Approved
0.7565	Intermediate Similarity	NPD6016	Approved
0.7551	Intermediate Similarity	NPD7524	Approved
0.7525	Intermediate Similarity	NPD8171	Discontinued
0.7521	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD5988	Approved
0.7458	Intermediate Similarity	NPD6616	Approved
0.7436	Intermediate Similarity	NPD6067	Discontinued
0.7423	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7319	Approved
0.7395	Intermediate Similarity	NPD7078	Approved
0.7391	Intermediate Similarity	NPD6942	Approved
0.7391	Intermediate Similarity	NPD7339	Approved
0.7364	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6695	Phase 3
0.7273	Intermediate Similarity	NPD6686	Approved
0.7263	Intermediate Similarity	NPD7645	Phase 2
0.7257	Intermediate Similarity	NPD8133	Approved
0.7217	Intermediate Similarity	NPD6009	Approved
0.719	Intermediate Similarity	NPD6033	Approved
0.7188	Intermediate Similarity	NPD6928	Phase 2
0.717	Intermediate Similarity	NPD7638	Approved
0.7168	Intermediate Similarity	NPD6882	Approved
0.7128	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6933	Approved
0.7117	Intermediate Similarity	NPD7320	Approved
0.7105	Intermediate Similarity	NPD4632	Approved
0.7103	Intermediate Similarity	NPD7639	Approved
0.7103	Intermediate Similarity	NPD7640	Approved
0.7097	Intermediate Similarity	NPD8449	Approved
0.7091	Intermediate Similarity	NPD7128	Approved
0.7091	Intermediate Similarity	NPD6402	Approved
0.7091	Intermediate Similarity	NPD5739	Approved
0.7091	Intermediate Similarity	NPD6675	Approved
0.704	Intermediate Similarity	NPD8450	Suspended
0.7034	Intermediate Similarity	NPD6319	Approved
0.703	Intermediate Similarity	NPD7750	Discontinued
0.703	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6399	Phase 3
0.7018	Intermediate Similarity	NPD8297	Approved
0.701	Intermediate Similarity	NPD6931	Approved
0.701	Intermediate Similarity	NPD6930	Phase 2
0.7	Intermediate Similarity	NPD8328	Phase 3
0.6964	Remote Similarity	NPD6881	Approved
0.6964	Remote Similarity	NPD6899	Approved
0.6937	Remote Similarity	NPD6008	Approved
0.6923	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4755	Approved
0.6915	Remote Similarity	NPD6924	Approved
0.6915	Remote Similarity	NPD6926	Approved
0.6907	Remote Similarity	NPD6929	Approved
0.6903	Remote Similarity	NPD6372	Approved
0.6903	Remote Similarity	NPD6373	Approved
0.69	Remote Similarity	NPD4786	Approved
0.6893	Remote Similarity	NPD5328	Approved
0.6882	Remote Similarity	NPD4243	Approved
0.6875	Remote Similarity	NPD5697	Approved
0.6875	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD6932	Approved
0.6857	Remote Similarity	NPD4202	Approved
0.6848	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4634	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6789	Remote Similarity	NPD4700	Approved
0.6789	Remote Similarity	NPD5286	Approved
0.6789	Remote Similarity	NPD4696	Approved
0.6789	Remote Similarity	NPD5285	Approved
0.6783	Remote Similarity	NPD8130	Phase 1
0.6783	Remote Similarity	NPD6650	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6649	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.678	Remote Similarity	NPD7115	Discovery
0.6765	Remote Similarity	NPD3618	Phase 1
0.6762	Remote Similarity	NPD6079	Approved
0.6762	Remote Similarity	NPD7087	Discontinued
0.6759	Remote Similarity	NPD6083	Phase 2
0.6759	Remote Similarity	NPD6084	Phase 2
0.6754	Remote Similarity	NPD6014	Approved
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6013	Approved
0.6754	Remote Similarity	NPD6012	Approved
0.6737	Remote Similarity	NPD4784	Approved
0.6737	Remote Similarity	NPD4785	Approved
0.6735	Remote Similarity	NPD6683	Phase 2
0.6721	Remote Similarity	NPD7604	Phase 2
0.6701	Remote Similarity	NPD5776	Phase 2
0.6701	Remote Similarity	NPD6925	Approved
0.67	Remote Similarity	NPD3667	Approved
0.6697	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD3168	Discontinued
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.6667	Remote Similarity	NPD5225	Approved
0.6638	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7145	Approved
0.6613	Remote Similarity	NPD6336	Discontinued
0.6607	Remote Similarity	NPD5174	Approved
0.6607	Remote Similarity	NPD5175	Approved
0.6604	Remote Similarity	NPD8035	Phase 2
0.6604	Remote Similarity	NPD8034	Phase 2
0.6577	Remote Similarity	NPD5223	Approved
0.6577	Remote Similarity	NPD4159	Approved
0.6574	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4753	Phase 2
0.6571	Remote Similarity	NPD6051	Approved
0.6562	Remote Similarity	NPD1810	Approved
0.6562	Remote Similarity	NPD1811	Approved
0.6557	Remote Similarity	NPD8517	Approved
0.6557	Remote Similarity	NPD8515	Approved
0.6557	Remote Similarity	NPD8513	Phase 3
0.6557	Remote Similarity	NPD8516	Approved
0.6549	Remote Similarity	NPD5141	Approved
0.6526	Remote Similarity	NPD7152	Approved
0.6526	Remote Similarity	NPD7151	Approved
0.6526	Remote Similarity	NPD7150	Approved
0.6518	Remote Similarity	NPD7632	Discontinued
0.6514	Remote Similarity	NPD5221	Approved
0.6514	Remote Similarity	NPD4697	Phase 3
0.6514	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5222	Approved
0.6505	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7332	Phase 2
0.6495	Remote Similarity	NPD5275	Approved
0.6495	Remote Similarity	NPD4190	Phase 3
0.6491	Remote Similarity	NPD4768	Approved
0.6491	Remote Similarity	NPD4767	Approved
0.6489	Remote Similarity	NPD6923	Approved
0.6489	Remote Similarity	NPD6922	Approved
0.6481	Remote Similarity	NPD7748	Approved
0.646	Remote Similarity	NPD4754	Approved
0.6455	Remote Similarity	NPD5173	Approved
0.6455	Remote Similarity	NPD7902	Approved
0.6449	Remote Similarity	NPD7515	Phase 2
0.6449	Remote Similarity	NPD7637	Suspended
0.6436	Remote Similarity	NPD6898	Phase 1
0.6436	Remote Similarity	NPD6902	Approved
0.6429	Remote Similarity	NPD5344	Discontinued
0.6423	Remote Similarity	NPD7625	Phase 1
0.6422	Remote Similarity	NPD5695	Phase 3
0.6421	Remote Similarity	NPD7143	Approved
0.6421	Remote Similarity	NPD7144	Approved
0.6417	Remote Similarity	NPD6274	Approved
0.641	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3133	Approved
0.6408	Remote Similarity	NPD3666	Approved
0.6408	Remote Similarity	NPD3665	Phase 1
0.64	Remote Similarity	NPD4195	Approved
0.6396	Remote Similarity	NPD5696	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6379	Remote Similarity	NPD5128	Approved
0.6379	Remote Similarity	NPD4730	Approved
0.6379	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4729	Approved
0.6321	Remote Similarity	NPD6903	Approved
0.6321	Remote Similarity	NPD6672	Approved
0.6321	Remote Similarity	NPD5737	Approved
0.6311	Remote Similarity	NPD6335	Approved
0.6303	Remote Similarity	NPD6053	Discontinued
0.629	Remote Similarity	NPD6909	Approved
0.629	Remote Similarity	NPD6908	Approved
0.629	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6409	Approved
0.6286	Remote Similarity	NPD7334	Approved
0.6286	Remote Similarity	NPD5330	Approved
0.6286	Remote Similarity	NPD6684	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