NPASS Compound

Structure

NPC31430 OpenBabel07101718322D 39 43 0 0 1 0 0 0 0 0999 V2000 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 4.3301 -4.5000 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 2 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 5.1962 -5.0000 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 4.3301 -3.5000 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 19 1 0 0 0 0 2 29 1 0 0 0 0 3 29 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 7 32 1 0 0 0 0 9 37 1 0 0 0 0 10 11 1 0 0 0 0 10 23 2 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 33 1 0 0 0 0 17 32 1 0 0 0 0 18 24 1 0 0 0 0 19 34 2 0 0 0 0 19 38 1 0 0 0 0 20 18 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 32 1 6 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 33 1 0 0 0 0 24 27 1 1 0 0 0 24 39 1 0 0 0 0 25 29 1 0 0 0 0 25 31 1 1 0 0 0 26 29 1 0 0 0 0 26 38 1 6 0 0 0 27 30 1 0 0 0 0 27 35 1 6 0 0 0 28 37 1 6 0 0 0 28 39 1 0 0 0 0 30 36 1 0 0 0 0 31 6 1 1 0 0 0 32 33 1 6 0 0 0 33 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.39
Volume:	584.01
LogP:	5.835
LogD:	4.705
LogS:	-4.998
# Rotatable Bonds:	6
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	5.159
Fsp3:	0.909
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:	-4.786
MDCK Permeability:	1.3835960999131203e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.655

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	94.0400161743164%
Volume Distribution (VD):	2.055
Pgp-substrate:	3.814514398574829%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.451
CYP3A4-substrate:	0.662

ADMET: Excretion

Clearance (CL):	3.558
Half-life (T1/2):	0.053

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.597
Maximum Recommended Daily Dose:	0.619
Skin Sensitization:	0.27
Carcinogencity:	0.041
Eye Corrosion:	0.005
Eye Irritation:	0.026
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: NPC31430

Natural Product ID:	NPC31430
*Common Name:**	Polystanin C
IUPAC Name:	[(3R,5R,9R,10R,13S,14S,17S)-17-[(2R,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:
Standard InCHIKey:	TYDCQDCBJWPAQE-OZUUNQNTSA-N
Standard InCHI:	InChI=1S/C33H54O6/c1-19(34)38-26-14-15-31(6)22-13-17-32(7)21(20-18-24(39-28(20)37-9)27(35)30(4,5)36)12-16-33(32,8)23(22)10-11-25(31)29(26,2)3/h10,20-22,24-28,35-36H,11-18H2,1-9H3/t20-,21-,22-,24+,25-,26+,27-,28+,31+,32-,33+/m0/s1
SMILES:	CC(=O)O[C@@H]1CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@]4(C)C3=CC[C@H]2C1(C)C)[C@@H]1C[C@H]([C@@H](C(C)(C)O)O)O[C@H]1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2392321
PubChem CID:	71531904
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
NPO3063	Aphanamixis grandifolia	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23772699]
NPO3063	Aphanamixis grandifolia	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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1800.0	nM	PMID[478957]

☑ 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 NPC31430 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	211
0.1-0.2	1475
0.2-0.3	5359
0.3-0.4	13132
0.4-0.5	8567
0.5-0.6	5749
0.6-0.7	5117
0.7-0.8	2564
0.8-0.85	452
0.85-0.9	65
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC85593
0.9505	High Similarity	NPC101450
0.9479	High Similarity	NPC216260
0.9479	High Similarity	NPC5358
0.9394	High Similarity	NPC470062
0.9394	High Similarity	NPC470059
0.9394	High Similarity	NPC470064
0.9394	High Similarity	NPC470057
0.9394	High Similarity	NPC470060
0.9394	High Similarity	NPC470061
0.9394	High Similarity	NPC470043
0.9394	High Similarity	NPC470058
0.93	High Similarity	NPC473199
0.9184	High Similarity	NPC324598
0.9118	High Similarity	NPC472988
0.9118	High Similarity	NPC38217
0.9109	High Similarity	NPC470055
0.9109	High Similarity	NPC470056
0.91	High Similarity	NPC213190
0.9048	High Similarity	NPC144068
0.9029	High Similarity	NPC154085
0.9029	High Similarity	NPC296761
0.9029	High Similarity	NPC125361
0.9029	High Similarity	NPC43976
0.9029	High Similarity	NPC51925
0.902	High Similarity	NPC234160
0.9	High Similarity	NPC154452
0.8932	High Similarity	NPC258323
0.8922	High Similarity	NPC63023
0.8922	High Similarity	NPC26798
0.8922	High Similarity	NPC95243
0.89	High Similarity	NPC129372
0.89	High Similarity	NPC160734
0.89	High Similarity	NPC21064
0.89	High Similarity	NPC88000
0.89	High Similarity	NPC121072
0.89	High Similarity	NPC309425
0.89	High Similarity	NPC47566
0.89	High Similarity	NPC4831
0.89	High Similarity	NPC472023
0.8889	High Similarity	NPC234287
0.8889	High Similarity	NPC280825
0.8879	High Similarity	NPC212660
0.8866	High Similarity	NPC96736
0.8866	High Similarity	NPC178949
0.8866	High Similarity	NPC211238
0.8857	High Similarity	NPC285410
0.8857	High Similarity	NPC250481
0.8857	High Similarity	NPC114188
0.8857	High Similarity	NPC65167
0.8857	High Similarity	NPC263827
0.8835	High Similarity	NPC226642
0.8824	High Similarity	NPC100955
0.8824	High Similarity	NPC121566
0.8824	High Similarity	NPC470885
0.8824	High Similarity	NPC187400
0.8824	High Similarity	NPC221562
0.8812	High Similarity	NPC136816
0.88	High Similarity	NPC473200
0.88	High Similarity	NPC7341
0.8788	High Similarity	NPC473890
0.8788	High Similarity	NPC243728
0.8776	High Similarity	NPC230347
0.8776	High Similarity	NPC275310
0.8776	High Similarity	NPC286612
0.8762	High Similarity	NPC103627
0.8762	High Similarity	NPC191439
0.8762	High Similarity	NPC170974
0.8762	High Similarity	NPC129340
0.875	High Similarity	NPC295980
0.875	High Similarity	NPC220427
0.875	High Similarity	NPC295389
0.8725	High Similarity	NPC471885
0.8725	High Similarity	NPC131479
0.8725	High Similarity	NPC471887
0.8725	High Similarity	NPC157659
0.8725	High Similarity	NPC475701
0.8725	High Similarity	NPC245280
0.8725	High Similarity	NPC286969
0.8725	High Similarity	NPC114874
0.8725	High Similarity	NPC155010
0.8725	High Similarity	NPC8039
0.8725	High Similarity	NPC471888
0.8725	High Similarity	NPC211879
0.8725	High Similarity	NPC120123
0.8725	High Similarity	NPC31907
0.8725	High Similarity	NPC189852
0.8725	High Similarity	NPC472252
0.8725	High Similarity	NPC16520
0.8725	High Similarity	NPC473020
0.8725	High Similarity	NPC471886
0.8713	High Similarity	NPC470054
0.8704	High Similarity	NPC63609
0.8704	High Similarity	NPC477031
0.8704	High Similarity	NPC146652
0.87	High Similarity	NPC477928
0.87	High Similarity	NPC158088
0.8679	High Similarity	NPC65034
0.8679	High Similarity	NPC208189
0.8679	High Similarity	NPC197231
0.8667	High Similarity	NPC473318
0.8667	High Similarity	NPC476835
0.8667	High Similarity	NPC265655
0.8667	High Similarity	NPC14630
0.8667	High Similarity	NPC157530
0.8667	High Similarity	NPC250089
0.8667	High Similarity	NPC28844
0.8667	High Similarity	NPC473328
0.8654	High Similarity	NPC190395
0.8641	High Similarity	NPC474464
0.8641	High Similarity	NPC475365
0.8641	High Similarity	NPC75608
0.8641	High Similarity	NPC273879
0.8641	High Similarity	NPC173583
0.8641	High Similarity	NPC165033
0.8636	High Similarity	NPC477071
0.8627	High Similarity	NPC37207
0.8627	High Similarity	NPC470053
0.8627	High Similarity	NPC159036
0.8627	High Similarity	NPC288694
0.8627	High Similarity	NPC312553
0.8624	High Similarity	NPC477807
0.8624	High Similarity	NPC203862
0.8624	High Similarity	NPC93883
0.8614	High Similarity	NPC317019
0.8614	High Similarity	NPC282669
0.8611	High Similarity	NPC69576
0.8611	High Similarity	NPC84949
0.8611	High Similarity	NPC477808
0.8611	High Similarity	NPC31354
0.8611	High Similarity	NPC473882
0.8611	High Similarity	NPC471633
0.86	High Similarity	NPC278939
0.86	High Similarity	NPC475032
0.86	High Similarity	NPC475033
0.86	High Similarity	NPC473555
0.86	High Similarity	NPC471770
0.8598	High Similarity	NPC231797
0.8598	High Similarity	NPC19888
0.8585	High Similarity	NPC154856
0.8585	High Similarity	NPC475317
0.8585	High Similarity	NPC65155
0.8585	High Similarity	NPC52241
0.8571	High Similarity	NPC476539
0.8571	High Similarity	NPC476540
0.8571	High Similarity	NPC195708
0.8571	High Similarity	NPC476541
0.8571	High Similarity	NPC476538
0.8558	High Similarity	NPC269627
0.8558	High Similarity	NPC472898
0.8558	High Similarity	NPC194842
0.8558	High Similarity	NPC470767
0.8558	High Similarity	NPC208477
0.8558	High Similarity	NPC127801
0.8558	High Similarity	NPC474015
0.8558	High Similarity	NPC160816
0.8558	High Similarity	NPC69737
0.8558	High Similarity	NPC242748
0.8558	High Similarity	NPC152584
0.8558	High Similarity	NPC472899
0.8558	High Similarity	NPC181845
0.8558	High Similarity	NPC472900
0.8558	High Similarity	NPC208594
0.8558	High Similarity	NPC470763
0.8558	High Similarity	NPC309448
0.8557	High Similarity	NPC473269
0.8545	High Similarity	NPC160888
0.8545	High Similarity	NPC475403
0.8544	High Similarity	NPC474124
0.8544	High Similarity	NPC473523
0.8544	High Similarity	NPC16573
0.8544	High Similarity	NPC473198
0.8532	High Similarity	NPC310341
0.8532	High Similarity	NPC199428
0.8532	High Similarity	NPC99620
0.8532	High Similarity	NPC193382
0.8532	High Similarity	NPC244127
0.8532	High Similarity	NPC5311
0.8529	High Similarity	NPC267510
0.8529	High Similarity	NPC475617
0.8529	High Similarity	NPC155974
0.8529	High Similarity	NPC470434
0.8519	High Similarity	NPC251309
0.8519	High Similarity	NPC476671
0.8515	High Similarity	NPC470067
0.8515	High Similarity	NPC102426
0.8515	High Similarity	NPC300179
0.8515	High Similarity	NPC157739
0.8515	High Similarity	NPC470068
0.8515	High Similarity	NPC470066
0.8515	High Similarity	NPC309493
0.8505	High Similarity	NPC272242
0.8505	High Similarity	NPC269466
0.8505	High Similarity	NPC292196
0.8505	High Similarity	NPC470748
0.85	High Similarity	NPC472989
0.85	High Similarity	NPC207617
0.8496	Intermediate Similarity	NPC41129
0.8491	Intermediate Similarity	NPC477026
0.8491	Intermediate Similarity	NPC40440

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 NPC31430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1739
0.2-0.3	4288
0.3-0.4	1975
0.4-0.5	486
0.5-0.6	227
0.6-0.7	197
0.7-0.8	65
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8393	Intermediate Similarity	NPD8377	Approved
0.8393	Intermediate Similarity	NPD8294	Approved
0.8378	Intermediate Similarity	NPD7327	Approved
0.8378	Intermediate Similarity	NPD7328	Approved
0.8319	Intermediate Similarity	NPD8380	Approved
0.8319	Intermediate Similarity	NPD8296	Approved
0.8319	Intermediate Similarity	NPD8379	Approved
0.8319	Intermediate Similarity	NPD8033	Approved
0.8319	Intermediate Similarity	NPD8335	Approved
0.8319	Intermediate Similarity	NPD8378	Approved
0.8304	Intermediate Similarity	NPD7516	Approved
0.812	Intermediate Similarity	NPD8293	Discontinued
0.8051	Intermediate Similarity	NPD7736	Approved
0.8	Intermediate Similarity	NPD7503	Approved
0.7963	Intermediate Similarity	NPD6412	Phase 2
0.7931	Intermediate Similarity	NPD6370	Approved
0.7881	Intermediate Similarity	NPD7507	Approved
0.7818	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7492	Approved
0.7759	Intermediate Similarity	NPD6059	Approved
0.7759	Intermediate Similarity	NPD6054	Approved
0.7731	Intermediate Similarity	NPD6616	Approved
0.7699	Intermediate Similarity	NPD8133	Approved
0.7686	Intermediate Similarity	NPD7319	Approved
0.7667	Intermediate Similarity	NPD7078	Approved
0.7568	Intermediate Similarity	NPD6686	Approved
0.7542	Intermediate Similarity	NPD6016	Approved
0.7542	Intermediate Similarity	NPD6015	Approved
0.7526	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD6009	Approved
0.7479	Intermediate Similarity	NPD5988	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7456	Intermediate Similarity	NPD8297	Approved
0.7456	Intermediate Similarity	NPD6882	Approved
0.7417	Intermediate Similarity	NPD8328	Phase 3
0.7417	Intermediate Similarity	NPD6067	Discontinued
0.7411	Intermediate Similarity	NPD7320	Approved
0.7407	Intermediate Similarity	NPD7640	Approved
0.7407	Intermediate Similarity	NPD7639	Approved
0.7391	Intermediate Similarity	NPD4632	Approved
0.7387	Intermediate Similarity	NPD7128	Approved
0.7387	Intermediate Similarity	NPD6675	Approved
0.7387	Intermediate Similarity	NPD6402	Approved
0.7387	Intermediate Similarity	NPD5739	Approved
0.735	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8171	Discontinued
0.7333	Intermediate Similarity	NPD6399	Phase 3
0.7311	Intermediate Similarity	NPD6319	Approved
0.7257	Intermediate Similarity	NPD6899	Approved
0.7257	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD6008	Approved
0.7217	Intermediate Similarity	NPD8130	Phase 1
0.7193	Intermediate Similarity	NPD6372	Approved
0.7193	Intermediate Similarity	NPD6373	Approved
0.7184	Intermediate Similarity	NPD7524	Approved
0.7177	Intermediate Similarity	NPD6033	Approved
0.7168	Intermediate Similarity	NPD5701	Approved
0.7168	Intermediate Similarity	NPD5697	Approved
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD8034	Phase 2
0.7075	Intermediate Similarity	NPD8035	Phase 2
0.7069	Intermediate Similarity	NPD6649	Approved
0.7069	Intermediate Similarity	NPD6847	Approved
0.7069	Intermediate Similarity	NPD6617	Approved
0.7069	Intermediate Similarity	NPD6650	Approved
0.7069	Intermediate Similarity	NPD6869	Approved
0.7064	Intermediate Similarity	NPD6083	Phase 2
0.7064	Intermediate Similarity	NPD6084	Phase 2
0.7059	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6014	Approved
0.7043	Intermediate Similarity	NPD6013	Approved
0.7043	Intermediate Similarity	NPD6012	Approved
0.701	Intermediate Similarity	NPD6942	Approved
0.701	Intermediate Similarity	NPD7339	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6992	Remote Similarity	NPD7604	Phase 2
0.6991	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5983	Phase 2
0.6967	Remote Similarity	NPD8513	Phase 3
0.6967	Remote Similarity	NPD8516	Approved
0.6967	Remote Similarity	NPD8517	Approved
0.6967	Remote Similarity	NPD8515	Approved
0.6961	Remote Similarity	NPD6695	Phase 3
0.6957	Remote Similarity	NPD6011	Approved
0.6953	Remote Similarity	NPD8449	Approved
0.6944	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7902	Approved
0.6909	Remote Similarity	NPD4755	Approved
0.69	Remote Similarity	NPD7645	Phase 2
0.6899	Remote Similarity	NPD8450	Suspended
0.6893	Remote Similarity	NPD4786	Approved
0.6887	Remote Similarity	NPD5328	Approved
0.6887	Remote Similarity	NPD6051	Approved
0.6881	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6336	Discontinued
0.6857	Remote Similarity	NPD7750	Discontinued
0.6852	Remote Similarity	NPD4202	Approved
0.6838	Remote Similarity	NPD4634	Approved
0.6832	Remote Similarity	NPD6928	Phase 2
0.6827	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7632	Discontinued
0.6786	Remote Similarity	NPD4700	Approved
0.6786	Remote Similarity	NPD4696	Approved
0.6786	Remote Similarity	NPD5286	Approved
0.6786	Remote Similarity	NPD5285	Approved
0.6768	Remote Similarity	NPD6933	Approved
0.6768	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3618	Phase 1
0.6759	Remote Similarity	NPD7515	Phase 2
0.6759	Remote Similarity	NPD7637	Suspended
0.6759	Remote Similarity	NPD6079	Approved
0.6727	Remote Similarity	NPD5695	Phase 3
0.6726	Remote Similarity	NPD5344	Discontinued
0.6699	Remote Similarity	NPD3667	Approved
0.6698	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5696	Approved
0.6695	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7625	Phase 1
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD5737	Approved
0.6636	Remote Similarity	NPD6903	Approved
0.6636	Remote Similarity	NPD7900	Approved
0.6636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6672	Approved
0.6609	Remote Similarity	NPD5174	Approved
0.6609	Remote Similarity	NPD5175	Approved
0.6604	Remote Similarity	NPD7334	Approved
0.6604	Remote Similarity	NPD6684	Approved
0.6604	Remote Similarity	NPD6409	Approved
0.6604	Remote Similarity	NPD7521	Approved
0.6604	Remote Similarity	NPD5330	Approved
0.6604	Remote Similarity	NPD7146	Approved
0.6585	Remote Similarity	NPD6335	Approved
0.6583	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD5223	Approved
0.6574	Remote Similarity	NPD4753	Phase 2
0.6569	Remote Similarity	NPD6929	Approved
0.6566	Remote Similarity	NPD6926	Approved
0.6566	Remote Similarity	NPD6924	Approved
0.656	Remote Similarity	NPD6908	Approved
0.656	Remote Similarity	NPD6909	Approved
0.656	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5141	Approved
0.6535	Remote Similarity	NPD6932	Approved
0.6531	Remote Similarity	NPD4243	Approved
0.6518	Remote Similarity	NPD5221	Approved
0.6518	Remote Similarity	NPD4697	Phase 3
0.6518	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5222	Approved
0.6504	Remote Similarity	NPD6317	Approved
0.65	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4768	Approved
0.6496	Remote Similarity	NPD4767	Approved
0.6495	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6001	Approved
0.6481	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6697	Approved
0.6471	Remote Similarity	NPD6115	Approved
0.6471	Remote Similarity	NPD6114	Approved
0.6471	Remote Similarity	NPD6118	Approved
0.6466	Remote Similarity	NPD4754	Approved
0.646	Remote Similarity	NPD5173	Approved
0.6455	Remote Similarity	NPD7087	Discontinued
0.6452	Remote Similarity	NPD6314	Approved
0.6452	Remote Similarity	NPD6313	Approved
0.6449	Remote Similarity	NPD6098	Approved
0.6441	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8074	Phase 3
0.6423	Remote Similarity	NPD6868	Approved
0.6422	Remote Similarity	NPD6904	Approved
0.6422	Remote Similarity	NPD6673	Approved
0.6422	Remote Similarity	NPD6080	Approved
0.6415	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3666	Approved
0.6415	Remote Similarity	NPD3665	Phase 1
0.6415	Remote Similarity	NPD3133	Approved
0.6408	Remote Similarity	NPD4195	Approved
0.6408	Remote Similarity	NPD6683	Phase 2
0.64	Remote Similarity	NPD4785	Approved
0.64	Remote Similarity	NPD4784	Approved
0.6387	Remote Similarity	NPD4729	Approved
0.6387	Remote Similarity	NPD5128	Approved
0.6387	Remote Similarity	NPD4730	Approved
0.6373	Remote Similarity	NPD5776	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