NPASS Compound

Structure

NPC475940 OpenBabel07101718232D 37 40 0 0 1 0 0 0 0 0999 V2000 5.7036 2.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 4.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 -1.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 -0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2199 2.4231 0.0000 C 0 0 0 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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -1.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 -1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 2.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 1.2070 0.0000 C 0 0 0 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 4.8376 3.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -1.2930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8376 0.2070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3689 1.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 3.9716 1.7070 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9716 -0.2930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2395 -0.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 1.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6744 0.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7436 -0.1340 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 10 13 2 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 12 34 1 0 0 0 0 14 3 1 6 0 0 0 14 22 1 0 0 0 0 15 4 1 6 0 0 0 15 20 1 0 0 0 0 16 23 2 0 0 0 0 16 27 1 0 0 0 0 17 30 2 0 0 0 0 17 35 1 0 0 0 0 18 31 2 0 0 0 0 18 36 1 0 0 0 0 19 10 1 6 0 0 0 19 23 1 0 0 0 0 20 9 1 1 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 21 35 1 1 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 25 28 1 0 0 0 0 25 32 1 1 0 0 0 26 27 2 0 0 0 0 26 33 1 0 0 0 0 27 37 1 0 0 0 0 28 29 1 0 0 0 0 28 36 1 6 0 0 0 29 34 1 0 0 0 0 29 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.27
Volume:	530.417
LogP:	5.202
LogD:	3.391
LogS:	-3.823
# Rotatable Bonds:	7
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	4.933
Fsp3:	0.655
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.01
MDCK Permeability:	4.643111242330633e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	0.074
30% Bioavailability (F30%):	0.236

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	95.11592864990234%
Volume Distribution (VD):	0.967
Pgp-substrate:	7.635136127471924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.168
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.395
CYP3A4-substrate:	0.568

ADMET: Excretion

Clearance (CL):	1.243
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.252
Human Hepatotoxicity (H-HT):	0.984
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.332
Rat Oral Acute Toxicity:	0.693
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.48
Carcinogencity:	0.149
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC475940

Natural Product ID:	NPC475940
*Common Name:**	Pseudopterosin X
IUPAC Name:	[(3R,4R,5S,6R)-5-acetyloxy-6-[[(4S,6S,6aR,9S)-1-hydroxy-3,6,9-trimethyl-4-(2-methylprop-1-enyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-2-yl]oxy]-4-hydroxyoxan-3-yl] acetate
Synonyms:	Pseudopterosin X
Standard InCHIKey:	OSDLXYTTXSGUFC-UMTNXJGOSA-N
Standard InCHI:	InChI=1S/C29H40O8/c1-13(2)10-19-11-15(4)20-9-8-14(3)22-24(20)23(19)16(5)27(26(22)33)37-29-28(36-18(7)31)25(32)21(12-34-29)35-17(6)30/h10,14-15,19-21,25,28-29,32-33H,8-9,11-12H2,1-7H3/t14-,15-,19+,20+,21+,25+,28-,29+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@H](OC[C@H]([C@H]1O)OC(=O)C)Oc1c(C)c2[C@H](C=C(C)C)C[C@@H]([C@@H]3c2c(c1O)[C@@H](C)CC3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519056
PubChem CID:	11352838
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003398] Amphilectane, neoamphilectane, cycloamphilectane, and adociane diterpenoids

*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
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[10425124]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10822593]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[11170678]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828474]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	Colombian	n.a.	PMID[15497938]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715964]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21978379]

☑ 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	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10000.0	nM	PMID[465890]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[465890]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.35	uM	PMID[465890]

☑ 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 NPC475940 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	330
0.1-0.2	1453
0.2-0.3	3509
0.3-0.4	7722
0.4-0.5	10051
0.5-0.6	6535
0.6-0.7	8785
0.7-0.8	3967
0.8-0.85	277
0.85-0.9	49
0.9-0.95	4
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474893
0.9929	High Similarity	NPC474834
0.9929	High Similarity	NPC290902
0.9929	High Similarity	NPC291326
0.9929	High Similarity	NPC117788
0.9929	High Similarity	NPC474856
0.9859	High Similarity	NPC181452
0.9859	High Similarity	NPC220006
0.965	High Similarity	NPC474940
0.965	High Similarity	NPC474795
0.965	High Similarity	NPC159697
0.965	High Similarity	NPC303013
0.965	High Similarity	NPC130959
0.9645	High Similarity	NPC133251
0.9384	High Similarity	NPC183380
0.9371	High Similarity	NPC164183
0.9247	High Similarity	NPC179809
0.9195	High Similarity	NPC200645
0.9195	High Similarity	NPC475227
0.9195	High Similarity	NPC106669
0.9156	High Similarity	NPC25889
0.9054	High Similarity	NPC44452
0.8973	High Similarity	NPC253015
0.8973	High Similarity	NPC471065
0.8912	High Similarity	NPC286245
0.8912	High Similarity	NPC272619
0.8896	High Similarity	NPC478269
0.8867	High Similarity	NPC469706
0.8867	High Similarity	NPC185955
0.8867	High Similarity	NPC214326
0.8867	High Similarity	NPC218041
0.8867	High Similarity	NPC9933
0.8867	High Similarity	NPC182368
0.8867	High Similarity	NPC145979
0.8867	High Similarity	NPC469707
0.8867	High Similarity	NPC225815
0.8867	High Similarity	NPC260781
0.8792	High Similarity	NPC193473
0.8792	High Similarity	NPC213074
0.8792	High Similarity	NPC275284
0.8792	High Similarity	NPC224674
0.8792	High Similarity	NPC31325
0.8792	High Similarity	NPC15956
0.8792	High Similarity	NPC114505
0.8782	High Similarity	NPC478267
0.8766	High Similarity	NPC228357
0.875	High Similarity	NPC21902
0.875	High Similarity	NPC474442
0.8658	High Similarity	NPC476301
0.8658	High Similarity	NPC43508
0.8627	High Similarity	NPC302610
0.8618	High Similarity	NPC24425
0.8618	High Similarity	NPC98624
0.8618	High Similarity	NPC472709
0.8618	High Similarity	NPC472710
0.8591	High Similarity	NPC217635
0.8591	High Similarity	NPC471667
0.8591	High Similarity	NPC79429
0.8537	High Similarity	NPC475054
0.8526	High Similarity	NPC11411
0.8523	High Similarity	NPC185307
0.8523	High Similarity	NPC470950
0.8506	High Similarity	NPC476452
0.8506	High Similarity	NPC478268
0.85	High Similarity	NPC222531
0.8493	Intermediate Similarity	NPC68292
0.8487	Intermediate Similarity	NPC95990
0.8477	Intermediate Similarity	NPC199928
0.8467	Intermediate Similarity	NPC283995
0.8467	Intermediate Similarity	NPC232228
0.8467	Intermediate Similarity	NPC470235
0.8467	Intermediate Similarity	NPC129417
0.8456	Intermediate Similarity	NPC131971
0.8456	Intermediate Similarity	NPC476356
0.8456	Intermediate Similarity	NPC253878
0.8452	Intermediate Similarity	NPC150442
0.8452	Intermediate Similarity	NPC299706
0.8452	Intermediate Similarity	NPC245615
0.8452	Intermediate Similarity	NPC115466
0.8452	Intermediate Similarity	NPC61604
0.8452	Intermediate Similarity	NPC78809
0.8446	Intermediate Similarity	NPC106944
0.8438	Intermediate Similarity	NPC14294
0.8438	Intermediate Similarity	NPC116759
0.8435	Intermediate Similarity	NPC138738
0.8435	Intermediate Similarity	NPC470413
0.8411	Intermediate Similarity	NPC252292
0.8411	Intermediate Similarity	NPC22150
0.8411	Intermediate Similarity	NPC475096
0.8411	Intermediate Similarity	NPC38041
0.8411	Intermediate Similarity	NPC476382
0.8411	Intermediate Similarity	NPC34587
0.8411	Intermediate Similarity	NPC100998
0.8411	Intermediate Similarity	NPC161700
0.8411	Intermediate Similarity	NPC34927
0.8411	Intermediate Similarity	NPC279298
0.8411	Intermediate Similarity	NPC277867
0.84	Intermediate Similarity	NPC478239
0.84	Intermediate Similarity	NPC46092
0.84	Intermediate Similarity	NPC113680
0.84	Intermediate Similarity	NPC278961
0.8395	Intermediate Similarity	NPC208818
0.8395	Intermediate Similarity	NPC185498
0.8389	Intermediate Similarity	NPC472711
0.8389	Intermediate Similarity	NPC471414
0.8387	Intermediate Similarity	NPC176186
0.8387	Intermediate Similarity	NPC169404
0.8387	Intermediate Similarity	NPC53587
0.8367	Intermediate Similarity	NPC199459
0.8367	Intermediate Similarity	NPC52277
0.8367	Intermediate Similarity	NPC177035
0.8366	Intermediate Similarity	NPC270751
0.8364	Intermediate Similarity	NPC193377
0.8355	Intermediate Similarity	NPC476865
0.8355	Intermediate Similarity	NPC125755
0.8355	Intermediate Similarity	NPC112861
0.8355	Intermediate Similarity	NPC471608
0.8355	Intermediate Similarity	NPC99515
0.8355	Intermediate Similarity	NPC190714
0.8344	Intermediate Similarity	NPC292443
0.8333	Intermediate Similarity	NPC157816
0.8333	Intermediate Similarity	NPC48309
0.8333	Intermediate Similarity	NPC469699
0.8333	Intermediate Similarity	NPC5262
0.8333	Intermediate Similarity	NPC140502
0.8333	Intermediate Similarity	NPC60249
0.8333	Intermediate Similarity	NPC472714
0.8333	Intermediate Similarity	NPC115203
0.8323	Intermediate Similarity	NPC2745
0.8313	Intermediate Similarity	NPC152424
0.8313	Intermediate Similarity	NPC115624
0.8313	Intermediate Similarity	NPC149873
0.8313	Intermediate Similarity	NPC7191
0.8313	Intermediate Similarity	NPC100465
0.8312	Intermediate Similarity	NPC106138
0.8311	Intermediate Similarity	NPC304152
0.8303	Intermediate Similarity	NPC316539
0.8302	Intermediate Similarity	NPC241600
0.8302	Intermediate Similarity	NPC173726
0.8301	Intermediate Similarity	NPC227902
0.8301	Intermediate Similarity	NPC39657
0.8301	Intermediate Similarity	NPC474397
0.8301	Intermediate Similarity	NPC232992
0.8293	Intermediate Similarity	NPC52598
0.8293	Intermediate Similarity	NPC179240
0.8291	Intermediate Similarity	NPC163635
0.8289	Intermediate Similarity	NPC476868
0.8289	Intermediate Similarity	NPC163898
0.8289	Intermediate Similarity	NPC476864
0.8289	Intermediate Similarity	NPC476869
0.8289	Intermediate Similarity	NPC18979
0.8289	Intermediate Similarity	NPC476866
0.8288	Intermediate Similarity	NPC227719
0.8282	Intermediate Similarity	NPC286809
0.8278	Intermediate Similarity	NPC37793
0.8278	Intermediate Similarity	NPC477898
0.8269	Intermediate Similarity	NPC471154
0.8269	Intermediate Similarity	NPC157783
0.8267	Intermediate Similarity	NPC186406
0.8267	Intermediate Similarity	NPC76871
0.8258	Intermediate Similarity	NPC158784
0.8258	Intermediate Similarity	NPC158635
0.8258	Intermediate Similarity	NPC195561
0.8258	Intermediate Similarity	NPC475224
0.8258	Intermediate Similarity	NPC229882
0.8255	Intermediate Similarity	NPC100389
0.825	Intermediate Similarity	NPC100936
0.825	Intermediate Similarity	NPC268718
0.825	Intermediate Similarity	NPC150943
0.825	Intermediate Similarity	NPC1253
0.825	Intermediate Similarity	NPC91634
0.8247	Intermediate Similarity	NPC248132
0.8247	Intermediate Similarity	NPC175976
0.8247	Intermediate Similarity	NPC130449
0.8247	Intermediate Similarity	NPC116229
0.8242	Intermediate Similarity	NPC312006
0.8242	Intermediate Similarity	NPC471920
0.8242	Intermediate Similarity	NPC129930
0.8242	Intermediate Similarity	NPC114550
0.8242	Intermediate Similarity	NPC471922
0.8242	Intermediate Similarity	NPC292712
0.8242	Intermediate Similarity	NPC20114
0.8242	Intermediate Similarity	NPC471921
0.8242	Intermediate Similarity	NPC474075
0.8235	Intermediate Similarity	NPC233980
0.8235	Intermediate Similarity	NPC474054
0.8231	Intermediate Similarity	NPC35731
0.8231	Intermediate Similarity	NPC476411
0.8231	Intermediate Similarity	NPC187194
0.8224	Intermediate Similarity	NPC472712
0.8224	Intermediate Similarity	NPC76176
0.8224	Intermediate Similarity	NPC138227
0.8224	Intermediate Similarity	NPC25292
0.8224	Intermediate Similarity	NPC84181
0.8224	Intermediate Similarity	NPC473108
0.8224	Intermediate Similarity	NPC476867
0.8224	Intermediate Similarity	NPC187774
0.8224	Intermediate Similarity	NPC473046
0.8224	Intermediate Similarity	NPC472713
0.8224	Intermediate Similarity	NPC168579

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 NPC475940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	923
0.2-0.3	2003
0.3-0.4	2759
0.4-0.5	1720
0.5-0.6	942
0.6-0.7	459
0.7-0.8	67
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
0.9433	High Similarity	NPD6674	Discontinued
0.8395	Intermediate Similarity	NPD7228	Approved
0.8187	Intermediate Similarity	NPD6234	Discontinued
0.8101	Intermediate Similarity	NPD37	Approved
0.8063	Intermediate Similarity	NPD4967	Phase 2
0.8063	Intermediate Similarity	NPD4965	Approved
0.8063	Intermediate Similarity	NPD4966	Approved
0.8013	Intermediate Similarity	NPD7266	Discontinued
0.7962	Intermediate Similarity	NPD1653	Approved
0.787	Intermediate Similarity	NPD7240	Approved
0.7852	Intermediate Similarity	NPD4060	Phase 1
0.7826	Intermediate Similarity	NPD8455	Phase 2
0.7778	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD8313	Approved
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD5844	Phase 1
0.7647	Intermediate Similarity	NPD7074	Phase 3
0.7616	Intermediate Similarity	NPD1613	Approved
0.7616	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3620	Phase 2
0.76	Intermediate Similarity	NPD7985	Registered
0.7588	Intermediate Similarity	NPD7054	Approved
0.7586	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7097	Phase 1
0.7564	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD5762	Approved
0.7548	Intermediate Similarity	NPD5763	Approved
0.7544	Intermediate Similarity	NPD7472	Approved
0.7516	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5124	Phase 1
0.744	Intermediate Similarity	NPD8127	Discontinued
0.7417	Intermediate Similarity	NPD3027	Phase 3
0.7414	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4140	Approved
0.7374	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7473	Discontinued
0.7368	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7685	Pre-registration
0.7356	Intermediate Similarity	NPD7251	Discontinued
0.7356	Intermediate Similarity	NPD6559	Discontinued
0.7351	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7680	Approved
0.7347	Intermediate Similarity	NPD3705	Approved
0.7347	Intermediate Similarity	NPD1091	Approved
0.7326	Intermediate Similarity	NPD3818	Discontinued
0.7314	Intermediate Similarity	NPD7808	Phase 3
0.7299	Intermediate Similarity	NPD6797	Phase 2
0.7294	Intermediate Similarity	NPD6232	Discontinued
0.7292	Intermediate Similarity	NPD7340	Approved
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7644	Approved
0.7237	Intermediate Similarity	NPD4908	Phase 1
0.7232	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5735	Approved
0.7222	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4626	Approved
0.7209	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6166	Phase 2
0.7209	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4625	Phase 3
0.7186	Intermediate Similarity	NPD1465	Phase 2
0.7186	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2861	Phase 2
0.716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1934	Approved
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7102	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5126	Approved
0.7095	Intermediate Similarity	NPD5125	Phase 3
0.7083	Intermediate Similarity	NPD1398	Phase 1
0.7081	Intermediate Similarity	NPD8166	Discontinued
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4110	Phase 3
0.7081	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7095	Approved
0.7076	Intermediate Similarity	NPD4666	Phase 3
0.7044	Intermediate Similarity	NPD2438	Suspended
0.7035	Intermediate Similarity	NPD6959	Discontinued
0.7032	Intermediate Similarity	NPD6798	Discontinued
0.702	Intermediate Similarity	NPD4749	Approved
0.7018	Intermediate Similarity	NPD5709	Phase 3
0.7017	Intermediate Similarity	NPD6843	Phase 3
0.7017	Intermediate Similarity	NPD7906	Approved
0.7017	Intermediate Similarity	NPD6841	Approved
0.7017	Intermediate Similarity	NPD6842	Approved
0.7012	Intermediate Similarity	NPD2532	Approved
0.7012	Intermediate Similarity	NPD2533	Approved
0.7012	Intermediate Similarity	NPD2534	Approved
0.7011	Intermediate Similarity	NPD2489	Approved
0.7011	Intermediate Similarity	NPD27	Approved
0.7	Intermediate Similarity	NPD1611	Approved
0.6995	Remote Similarity	NPD7783	Phase 2
0.6995	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3787	Discontinued
0.6994	Remote Similarity	NPD3051	Approved
0.6994	Remote Similarity	NPD5058	Phase 3
0.6984	Remote Similarity	NPD7435	Discontinued
0.6983	Remote Similarity	NPD7312	Approved
0.6983	Remote Similarity	NPD7311	Approved
0.6983	Remote Similarity	NPD7310	Approved
0.6983	Remote Similarity	NPD7313	Approved
0.6982	Remote Similarity	NPD7819	Suspended
0.6981	Remote Similarity	NPD4108	Discontinued
0.6979	Remote Similarity	NPD8151	Discontinued
0.6975	Remote Similarity	NPD4628	Phase 3
0.6974	Remote Similarity	NPD6696	Suspended
0.6974	Remote Similarity	NPD8651	Approved
0.6962	Remote Similarity	NPD6653	Approved
0.6961	Remote Similarity	NPD4663	Approved
0.6959	Remote Similarity	NPD7075	Discontinued
0.6954	Remote Similarity	NPD2970	Approved
0.6954	Remote Similarity	NPD2969	Approved
0.6944	Remote Similarity	NPD7309	Approved
0.6937	Remote Similarity	NPD6099	Approved
0.6937	Remote Similarity	NPD6100	Approved
0.6914	Remote Similarity	NPD4481	Phase 3
0.6913	Remote Similarity	NPD1357	Approved
0.6909	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5327	Phase 3
0.6894	Remote Similarity	NPD6004	Phase 3
0.6894	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6005	Phase 3
0.6894	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6002	Phase 3
0.6894	Remote Similarity	NPD2346	Discontinued
0.6889	Remote Similarity	NPD4577	Approved
0.6889	Remote Similarity	NPD4578	Approved
0.6887	Remote Similarity	NPD1610	Phase 2
0.6883	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6233	Phase 2
0.6871	Remote Similarity	NPD7157	Approved
0.6867	Remote Similarity	NPD6273	Approved
0.6867	Remote Similarity	NPD2676	Approved
0.6867	Remote Similarity	NPD2675	Approved
0.6863	Remote Similarity	NPD1283	Approved
0.6849	Remote Similarity	NPD5283	Phase 1
0.6848	Remote Similarity	NPD7041	Phase 2
0.6848	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3226	Approved
0.6842	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6823	Phase 2
0.6842	Remote Similarity	NPD3817	Phase 2
0.6839	Remote Similarity	NPD5736	Approved
0.6836	Remote Similarity	NPD3751	Discontinued
0.6835	Remote Similarity	NPD2979	Phase 3
0.6833	Remote Similarity	NPD7549	Discontinued
0.6829	Remote Similarity	NPD6190	Approved
0.6828	Remote Similarity	NPD228	Approved
0.6825	Remote Similarity	NPD6782	Approved
0.6825	Remote Similarity	NPD6781	Approved
0.6825	Remote Similarity	NPD6777	Approved
0.6825	Remote Similarity	NPD6780	Approved
0.6825	Remote Similarity	NPD6779	Approved
0.6825	Remote Similarity	NPD6778	Approved
0.6825	Remote Similarity	NPD6776	Approved
0.6818	Remote Similarity	NPD3094	Phase 2
0.6813	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4536	Approved
0.6813	Remote Similarity	NPD4538	Approved
0.681	Remote Similarity	NPD1652	Phase 2
0.6805	Remote Similarity	NPD7028	Phase 2
0.6805	Remote Similarity	NPD4380	Phase 2
0.68	Remote Similarity	NPD7229	Phase 3
0.6797	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3657	Discovery
0.679	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6667	Approved
0.6788	Remote Similarity	NPD6666	Approved
0.6784	Remote Similarity	NPD2801	Approved
0.6784	Remote Similarity	NPD5929	Approved
0.6784	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5494	Approved
0.6781	Remote Similarity	NPD7843	Approved
0.6776	Remote Similarity	NPD8150	Discontinued
0.6772	Remote Similarity	NPD8032	Phase 2
0.6769	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7874	Approved
0.6768	Remote Similarity	NPD7003	Approved
0.6766	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6671	Approved
0.6755	Remote Similarity	NPD1778	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