NPASS Compound

Structure

NPC117788 OpenBabel07101719512D 34 37 0 0 1 0 0 0 0 0999 V2000 5.5928 1.2287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7268 2.7287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2627 -3.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5928 -1.7713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1091 0.9448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5053 -0.8379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9948 -3.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8608 -2.7713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8608 1.2287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7268 -0.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7268 1.7287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1287 -2.7713 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7268 -1.2713 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2582 -0.0441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5745 -0.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8608 0.2287 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8608 -1.7713 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7127 0.2581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1287 -1.7713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9948 -0.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9948 -1.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 -0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0799 -1.3542 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8617 -0.7307 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5637 -1.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1490 -0.9888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4254 0.5163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4945 0.8816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7552 0.0217 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2290 -2.3430 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 -2.7926 -1.0960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6328 -1.6123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 9 12 2 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 11 32 1 0 0 0 0 13 3 1 6 0 0 0 13 20 1 0 0 0 0 14 4 1 6 0 0 0 14 18 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 28 2 0 0 0 0 16 33 1 0 0 0 0 17 9 1 1 0 0 0 17 21 1 0 0 0 0 18 8 1 1 0 0 0 18 22 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 6 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 23 26 2 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 24 31 1 6 0 0 0 25 33 1 1 0 0 0 26 34 1 0 0 0 0 27 32 1 0 0 0 0 27 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.26
Volume:	489.672
LogP:	4.76
LogD:	3.062
LogS:	-3.845
# Rotatable Bonds:	5
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	4.951
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973
MDCK Permeability:	2.5054609068320133e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	96.85072326660156%
Volume Distribution (VD):	1.147
Pgp-substrate:	7.344645977020264%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.175
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.317
CYP3A4-substrate:	0.332

ADMET: Excretion

Clearance (CL):	1.357
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.869
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.463
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC117788

Natural Product ID:	NPC117788
*Common Name:**	Pseudopterosin C
IUPAC Name:	[(2S,3R,4S,5R)-2-[[(4R,6S,6aR,9S)-2-hydroxy-3,6,9-trimethyl-4-(2-methylprop-1-enyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl]oxy]-3,5-dihydroxyoxan-4-yl] acetate
Synonyms:	Pseudopterosin C
Standard InCHIKey:	KFGFLTUAFJTHSD-HPZAAEPWSA-N
Standard InCHI:	InChI=1S/C27H38O7/c1-12(2)9-17-10-14(4)18-8-7-13(3)20-22(18)21(17)15(5)23(30)26(20)34-27-24(31)25(33-16(6)28)19(29)11-32-27/h9,13-14,17-19,24-25,27,29-31H,7-8,10-11H2,1-6H3/t13-,14-,17-,18+,19+,24+,25-,27-/m0/s1
SMILES:	CC(=C[C@H]1C[C@H](C)[C@H]2CC[C@H](C)c3c2c1c(C)c(c3O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)OC(=O)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478977
PubChem CID:	21637884
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene 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
NPO33065	Pseudopterogorgia	Genus	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2895165]

☑ 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
ED50	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	75.0	%	PMID[517628]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	10.0	mg.kg-1	PMID[517628]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	4.0	mg.kg-1	PMID[517628]

☑ 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 NPC117788 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	324
0.1-0.2	1456
0.2-0.3	3474
0.3-0.4	7710
0.4-0.5	10228
0.5-0.6	6286
0.6-0.7	8913
0.7-0.8	4000
0.8-0.85	244
0.85-0.9	43
0.9-0.95	4
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474856
1.0	High Similarity	NPC474834
1.0	High Similarity	NPC290902
1.0	High Similarity	NPC291326
0.9929	High Similarity	NPC475940
0.9929	High Similarity	NPC474893
0.9929	High Similarity	NPC220006
0.9929	High Similarity	NPC181452
0.9718	High Similarity	NPC474940
0.9718	High Similarity	NPC303013
0.9718	High Similarity	NPC130959
0.9718	High Similarity	NPC474795
0.9718	High Similarity	NPC159697
0.9714	High Similarity	NPC133251
0.9437	High Similarity	NPC164183
0.9315	High Similarity	NPC183380
0.9178	High Similarity	NPC179809
0.9128	High Similarity	NPC200645
0.9128	High Similarity	NPC106669
0.9128	High Similarity	NPC475227
0.9091	High Similarity	NPC25889
0.8986	High Similarity	NPC44452
0.8904	High Similarity	NPC471065
0.8904	High Similarity	NPC253015
0.8844	High Similarity	NPC272619
0.8844	High Similarity	NPC286245
0.8831	High Similarity	NPC478269
0.88	High Similarity	NPC225815
0.88	High Similarity	NPC218041
0.88	High Similarity	NPC9933
0.88	High Similarity	NPC214326
0.88	High Similarity	NPC145979
0.88	High Similarity	NPC185955
0.88	High Similarity	NPC260781
0.88	High Similarity	NPC469707
0.88	High Similarity	NPC469706
0.88	High Similarity	NPC182368
0.8725	High Similarity	NPC31325
0.8725	High Similarity	NPC224674
0.8725	High Similarity	NPC114505
0.8725	High Similarity	NPC275284
0.8725	High Similarity	NPC213074
0.8725	High Similarity	NPC15956
0.8725	High Similarity	NPC193473
0.8718	High Similarity	NPC478267
0.8701	High Similarity	NPC228357
0.8684	High Similarity	NPC474442
0.8684	High Similarity	NPC21902
0.8591	High Similarity	NPC476301
0.8591	High Similarity	NPC43508
0.8562	High Similarity	NPC476452
0.8562	High Similarity	NPC302610
0.8553	High Similarity	NPC24425
0.8553	High Similarity	NPC472710
0.8553	High Similarity	NPC472709
0.8553	High Similarity	NPC98624
0.8552	High Similarity	NPC68292
0.8543	High Similarity	NPC95990
0.8523	High Similarity	NPC471667
0.8523	High Similarity	NPC79429
0.8523	High Similarity	NPC217635
0.8514	High Similarity	NPC253878
0.8476	Intermediate Similarity	NPC475054
0.8462	Intermediate Similarity	NPC11411
0.8456	Intermediate Similarity	NPC185307
0.8456	Intermediate Similarity	NPC470950
0.8446	Intermediate Similarity	NPC471414
0.8442	Intermediate Similarity	NPC478268
0.8438	Intermediate Similarity	NPC222531
0.8411	Intermediate Similarity	NPC199928
0.8411	Intermediate Similarity	NPC471608
0.84	Intermediate Similarity	NPC129417
0.84	Intermediate Similarity	NPC232228
0.84	Intermediate Similarity	NPC283995
0.84	Intermediate Similarity	NPC470235
0.8389	Intermediate Similarity	NPC131971
0.8389	Intermediate Similarity	NPC476356
0.8387	Intermediate Similarity	NPC245615
0.8387	Intermediate Similarity	NPC150442
0.8387	Intermediate Similarity	NPC115466
0.8387	Intermediate Similarity	NPC78809
0.8387	Intermediate Similarity	NPC299706
0.8387	Intermediate Similarity	NPC61604
0.8378	Intermediate Similarity	NPC106944
0.8377	Intermediate Similarity	NPC2745
0.8375	Intermediate Similarity	NPC14294
0.8375	Intermediate Similarity	NPC116759
0.8367	Intermediate Similarity	NPC138738
0.8367	Intermediate Similarity	NPC470413
0.8355	Intermediate Similarity	NPC474397
0.8345	Intermediate Similarity	NPC227719
0.8344	Intermediate Similarity	NPC34587
0.8344	Intermediate Similarity	NPC279298
0.8344	Intermediate Similarity	NPC252292
0.8344	Intermediate Similarity	NPC163898
0.8344	Intermediate Similarity	NPC476382
0.8344	Intermediate Similarity	NPC34927
0.8344	Intermediate Similarity	NPC22150
0.8344	Intermediate Similarity	NPC100998
0.8344	Intermediate Similarity	NPC475096
0.8344	Intermediate Similarity	NPC277867
0.8344	Intermediate Similarity	NPC161700
0.8344	Intermediate Similarity	NPC38041
0.8333	Intermediate Similarity	NPC208818
0.8333	Intermediate Similarity	NPC46092
0.8333	Intermediate Similarity	NPC185498
0.8333	Intermediate Similarity	NPC113680
0.8333	Intermediate Similarity	NPC278961
0.8333	Intermediate Similarity	NPC478239
0.8323	Intermediate Similarity	NPC176186
0.8323	Intermediate Similarity	NPC169404
0.8323	Intermediate Similarity	NPC157783
0.8323	Intermediate Similarity	NPC53587
0.8322	Intermediate Similarity	NPC472711
0.8312	Intermediate Similarity	NPC195561
0.8312	Intermediate Similarity	NPC158784
0.8303	Intermediate Similarity	NPC193377
0.8301	Intermediate Similarity	NPC270751
0.8299	Intermediate Similarity	NPC52277
0.8299	Intermediate Similarity	NPC177035
0.8299	Intermediate Similarity	NPC199459
0.8289	Intermediate Similarity	NPC112861
0.8289	Intermediate Similarity	NPC125755
0.8289	Intermediate Similarity	NPC99515
0.8289	Intermediate Similarity	NPC190714
0.8289	Intermediate Similarity	NPC233980
0.8289	Intermediate Similarity	NPC476865
0.8278	Intermediate Similarity	NPC292443
0.8278	Intermediate Similarity	NPC473108
0.8269	Intermediate Similarity	NPC115203
0.8269	Intermediate Similarity	NPC469699
0.8267	Intermediate Similarity	NPC140502
0.8267	Intermediate Similarity	NPC48309
0.8267	Intermediate Similarity	NPC157816
0.8267	Intermediate Similarity	NPC60249
0.8267	Intermediate Similarity	NPC472714
0.8267	Intermediate Similarity	NPC5262
0.8258	Intermediate Similarity	NPC302915
0.825	Intermediate Similarity	NPC149873
0.825	Intermediate Similarity	NPC152424
0.825	Intermediate Similarity	NPC100465
0.825	Intermediate Similarity	NPC7191
0.825	Intermediate Similarity	NPC115624
0.8247	Intermediate Similarity	NPC106138
0.8247	Intermediate Similarity	NPC10010
0.8243	Intermediate Similarity	NPC304152
0.8242	Intermediate Similarity	NPC316539
0.8239	Intermediate Similarity	NPC241600
0.8239	Intermediate Similarity	NPC173726
0.8235	Intermediate Similarity	NPC227902
0.8235	Intermediate Similarity	NPC232992
0.8235	Intermediate Similarity	NPC39657
0.8232	Intermediate Similarity	NPC52598
0.8232	Intermediate Similarity	NPC179240
0.8228	Intermediate Similarity	NPC163635
0.8224	Intermediate Similarity	NPC476869
0.8224	Intermediate Similarity	NPC476868
0.8224	Intermediate Similarity	NPC18979
0.8224	Intermediate Similarity	NPC476864
0.8224	Intermediate Similarity	NPC476866
0.8221	Intermediate Similarity	NPC286809
0.8212	Intermediate Similarity	NPC37793
0.8212	Intermediate Similarity	NPC472451
0.8212	Intermediate Similarity	NPC477898
0.8207	Intermediate Similarity	NPC312341
0.8205	Intermediate Similarity	NPC471154
0.8205	Intermediate Similarity	NPC325860
0.8205	Intermediate Similarity	NPC160196
0.82	Intermediate Similarity	NPC76871
0.82	Intermediate Similarity	NPC186406
0.82	Intermediate Similarity	NPC265075
0.8194	Intermediate Similarity	NPC229882
0.8194	Intermediate Similarity	NPC475224
0.8194	Intermediate Similarity	NPC158635
0.8188	Intermediate Similarity	NPC100389
0.8187	Intermediate Similarity	NPC268718
0.8187	Intermediate Similarity	NPC150943
0.8187	Intermediate Similarity	NPC91634
0.8187	Intermediate Similarity	NPC1253
0.8187	Intermediate Similarity	NPC100936
0.8182	Intermediate Similarity	NPC114550
0.8182	Intermediate Similarity	NPC248132
0.8182	Intermediate Similarity	NPC471922
0.8182	Intermediate Similarity	NPC312006
0.8182	Intermediate Similarity	NPC212142
0.8182	Intermediate Similarity	NPC292712
0.8182	Intermediate Similarity	NPC129930
0.8182	Intermediate Similarity	NPC20114
0.8182	Intermediate Similarity	NPC474075
0.8182	Intermediate Similarity	NPC471921
0.8182	Intermediate Similarity	NPC471920
0.8182	Intermediate Similarity	NPC175976
0.8182	Intermediate Similarity	NPC470757
0.8182	Intermediate Similarity	NPC116229
0.8182	Intermediate Similarity	NPC130449
0.8182	Intermediate Similarity	NPC473876
0.8176	Intermediate Similarity	NPC156502
0.8176	Intermediate Similarity	NPC209985
0.8176	Intermediate Similarity	NPC263367
0.8176	Intermediate Similarity	NPC29799

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 NPC117788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	926
0.2-0.3	1993
0.3-0.4	2741
0.4-0.5	1723
0.5-0.6	957
0.6-0.7	463
0.7-0.8	76
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.95	High Similarity	NPD6674	Discontinued
0.8333	Intermediate Similarity	NPD7228	Approved
0.8125	Intermediate Similarity	NPD6234	Discontinued
0.8038	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD4965	Approved
0.7947	Intermediate Similarity	NPD7266	Discontinued
0.7905	Intermediate Similarity	NPD4060	Phase 1
0.7898	Intermediate Similarity	NPD1653	Approved
0.7811	Intermediate Similarity	NPD7240	Approved
0.7764	Intermediate Similarity	NPD8455	Phase 2
0.7738	Intermediate Similarity	NPD5844	Phase 1
0.7719	Intermediate Similarity	NPD8312	Approved
0.7719	Intermediate Similarity	NPD8313	Approved
0.7697	Intermediate Similarity	NPD7199	Phase 2
0.7667	Intermediate Similarity	NPD3620	Phase 2
0.7667	Intermediate Similarity	NPD1613	Approved
0.7667	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7985	Registered
0.7613	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5762	Approved
0.7597	Intermediate Similarity	NPD5763	Approved
0.7588	Intermediate Similarity	NPD7074	Phase 3
0.7529	Intermediate Similarity	NPD7054	Approved
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7472	Approved
0.7467	Intermediate Similarity	NPD3027	Phase 3
0.7459	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4140	Approved
0.7417	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1091	Approved
0.7397	Intermediate Similarity	NPD3705	Approved
0.7381	Intermediate Similarity	NPD8127	Discontinued
0.7356	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7340	Approved
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7473	Discontinued
0.7303	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7685	Pre-registration
0.7299	Intermediate Similarity	NPD7251	Discontinued
0.7299	Intermediate Similarity	NPD6559	Discontinued
0.7297	Intermediate Similarity	NPD7680	Approved
0.7292	Intermediate Similarity	NPD7644	Approved
0.7285	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD5735	Approved
0.7273	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3818	Discontinued
0.726	Intermediate Similarity	NPD4626	Approved
0.7257	Intermediate Similarity	NPD7808	Phase 3
0.7241	Intermediate Similarity	NPD6797	Phase 2
0.7237	Intermediate Similarity	NPD4625	Phase 3
0.7235	Intermediate Similarity	NPD6232	Discontinued
0.7229	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7192	Intermediate Similarity	NPD5691	Approved
0.719	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1934	Approved
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.7151	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD5125	Phase 3
0.7143	Intermediate Similarity	NPD5126	Approved
0.7133	Intermediate Similarity	NPD1398	Phase 1
0.7126	Intermediate Similarity	NPD1465	Phase 2
0.7126	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD8166	Discontinued
0.7125	Intermediate Similarity	NPD4110	Phase 3
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7095	Approved
0.7118	Intermediate Similarity	NPD4666	Phase 3
0.7101	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6798	Discontinued
0.7067	Intermediate Similarity	NPD4749	Approved
0.7059	Intermediate Similarity	NPD5709	Phase 3
0.7055	Intermediate Similarity	NPD2532	Approved
0.7055	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD2533	Approved
0.7052	Intermediate Similarity	NPD2489	Approved
0.7052	Intermediate Similarity	NPD27	Approved
0.7047	Intermediate Similarity	NPD1611	Approved
0.7045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5058	Phase 3
0.7035	Intermediate Similarity	NPD3051	Approved
0.7035	Intermediate Similarity	NPD3787	Discontinued
0.7025	Intermediate Similarity	NPD4108	Discontinued
0.7022	Intermediate Similarity	NPD7311	Approved
0.7022	Intermediate Similarity	NPD7310	Approved
0.7022	Intermediate Similarity	NPD7313	Approved
0.7022	Intermediate Similarity	NPD7312	Approved
0.702	Intermediate Similarity	NPD8651	Approved
0.702	Intermediate Similarity	NPD6696	Suspended
0.7019	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD4663	Approved
0.6994	Remote Similarity	NPD2970	Approved
0.6994	Remote Similarity	NPD2969	Approved
0.6983	Remote Similarity	NPD7309	Approved
0.6981	Remote Similarity	NPD2438	Suspended
0.6981	Remote Similarity	NPD6099	Approved
0.6981	Remote Similarity	NPD6100	Approved
0.6977	Remote Similarity	NPD6959	Discontinued
0.6961	Remote Similarity	NPD6841	Approved
0.6961	Remote Similarity	NPD6843	Phase 3
0.6961	Remote Similarity	NPD6842	Approved
0.6961	Remote Similarity	NPD7906	Approved
0.6959	Remote Similarity	NPD1357	Approved
0.6954	Remote Similarity	NPD4481	Phase 3
0.6954	Remote Similarity	NPD5327	Phase 3
0.6954	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7783	Phase 2
0.6943	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6004	Phase 3
0.6937	Remote Similarity	NPD2346	Discontinued
0.6937	Remote Similarity	NPD6002	Phase 3
0.6937	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD1610	Phase 2
0.6931	Remote Similarity	NPD7435	Discontinued
0.6928	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4578	Approved
0.6927	Remote Similarity	NPD8151	Discontinued
0.6927	Remote Similarity	NPD4577	Approved
0.6923	Remote Similarity	NPD6233	Phase 2
0.6923	Remote Similarity	NPD7819	Suspended
0.6909	Remote Similarity	NPD6273	Approved
0.6909	Remote Similarity	NPD2675	Approved
0.6909	Remote Similarity	NPD2676	Approved
0.6908	Remote Similarity	NPD1283	Approved
0.6901	Remote Similarity	NPD7075	Discontinued
0.6897	Remote Similarity	NPD5283	Phase 1
0.689	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7041	Phase 2
0.6883	Remote Similarity	NPD5736	Approved
0.6879	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD228	Approved
0.6872	Remote Similarity	NPD7549	Discontinued
0.6863	Remote Similarity	NPD3094	Phase 2
0.6855	Remote Similarity	NPD4536	Approved
0.6855	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4538	Approved
0.6852	Remote Similarity	NPD1652	Phase 2
0.6848	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7028	Phase 2
0.6842	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7229	Phase 3
0.6835	Remote Similarity	NPD3657	Discovery
0.6832	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6666	Approved
0.6829	Remote Similarity	NPD6667	Approved
0.6824	Remote Similarity	NPD5929	Approved
0.6824	Remote Similarity	NPD2801	Approved
0.6824	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5494	Approved
0.6815	Remote Similarity	NPD8032	Phase 2
0.681	Remote Similarity	NPD7003	Approved
0.6807	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7157	Approved
0.6803	Remote Similarity	NPD6671	Approved
0.68	Remote Similarity	NPD1778	Approved
0.6792	Remote Similarity	NPD6353	Approved
0.6792	Remote Similarity	NPD4097	Suspended
0.679	Remote Similarity	NPD2424	Discontinued
0.6789	Remote Similarity	NPD6823	Phase 2
0.6786	Remote Similarity	NPD3226	Approved
0.6784	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3817	Phase 2
0.6772	Remote Similarity	NPD6782	Approved
0.6772	Remote Similarity	NPD6776	Approved
0.6772	Remote Similarity	NPD6779	Approved
0.6772	Remote Similarity	NPD6778	Approved
0.6772	Remote Similarity	NPD6777	Approved
0.6772	Remote Similarity	NPD6781	Approved
0.6772	Remote Similarity	NPD6780	Approved
0.6768	Remote Similarity	NPD2677	Approved
0.6768	Remote Similarity	NPD6190	Approved
0.6765	Remote Similarity	NPD7945	Clinical (unspecified phase)

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