NPASS Compound

Structure

NPC159697 OpenBabel07101719512D 34 36 0 0 1 0 0 0 0 0999 V2000 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 -2.5981 -1.5000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 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 -2.5981 1.5000 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 1.7321 1.0000 0.0000 C 0 0 2 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 1 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 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 0.0000 0.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 32 1 0 0 0 0 15 3 1 6 0 0 0 16 4 1 6 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 28 2 0 0 0 0 18 33 1 0 0 0 0 19 15 1 1 0 0 0 19 20 1 0 0 0 0 20 22 2 0 0 0 0 21 24 1 0 0 0 0 21 29 1 6 0 0 0 22 25 1 0 0 0 0 23 25 2 0 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 6 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 26 33 1 1 0 0 0 27 32 1 0 0 0 0 27 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.28
Volume:	498.228
LogP:	5.258
LogD:	3.717
LogS:	-3.652
# Rotatable Bonds:	8
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	4.69
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:	-4.868
MDCK Permeability:	2.3097347366274334e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	97.10939025878906%
Volume Distribution (VD):	0.968
Pgp-substrate:	5.856851100921631%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.089
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.173
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.337
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	3.322
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.305
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.395
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.811
Carcinogencity:	0.134
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC159697

Natural Product ID:	NPC159697
*Common Name:**	Seco-Pseudopterosin B
IUPAC Name:	[(2S,3S,4R,5R)-4,5-dihydroxy-2-[[(5R,8S)-2-hydroxy-3,8-dimethyl-5-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]oxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	HZIKKERDFPWVLN-KMQDHLQASA-N
Standard InCHI:	InChI=1S/C27H40O7/c1-14(2)8-7-9-15(3)19-11-10-16(4)22-20(19)12-17(5)23(30)25(22)34-27-26(33-18(6)28)24(31)21(29)13-32-27/h8,12,15-16,19,21,24,26-27,29-31H,7,9-11,13H2,1-6H3/t15-,16-,19+,21+,24+,26-,27-/m0/s1
SMILES:	CC(=CCC[C@H](C)[C@H]1CC[C@H](C)c2c1cc(C)c(c2O[C@H]1[C@H]([C@@H]([C@@H](CO1)O)O)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515959
PubChem CID:	44584537
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
Others	1

Activity Type	# Activity
Organism	1

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[450096]

☑ 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 NPC159697 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	329
0.1-0.2	1433
0.2-0.3	3373
0.3-0.4	7985
0.4-0.5	10182
0.5-0.6	5351
0.6-0.7	8807
0.7-0.8	4703
0.8-0.85	452
0.85-0.9	64
0.9-0.95	3
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474940
1.0	High Similarity	NPC130959
1.0	High Similarity	NPC303013
1.0	High Similarity	NPC474795
0.9718	High Similarity	NPC290902
0.9718	High Similarity	NPC291326
0.9718	High Similarity	NPC474834
0.9718	High Similarity	NPC117788
0.9718	High Similarity	NPC474856
0.9714	High Similarity	NPC164183
0.965	High Similarity	NPC474893
0.965	High Similarity	NPC475940
0.965	High Similarity	NPC181452
0.965	High Similarity	NPC220006
0.9437	High Similarity	NPC133251
0.9315	High Similarity	NPC183380
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
0.898	High Similarity	NPC193473
0.898	High Similarity	NPC15956
0.898	High Similarity	NPC275284
0.898	High Similarity	NPC224674
0.898	High Similarity	NPC213074
0.898	High Similarity	NPC114505
0.898	High Similarity	NPC31325
0.8947	High Similarity	NPC228357
0.8919	High Similarity	NPC179809
0.8904	High Similarity	NPC471065
0.8904	High Similarity	NPC253015
0.8844	High Similarity	NPC43508
0.8844	High Similarity	NPC476301
0.8844	High Similarity	NPC272619
0.8844	High Similarity	NPC286245
0.8831	High Similarity	NPC478269
0.8808	High Similarity	NPC302610
0.88	High Similarity	NPC472709
0.88	High Similarity	NPC225815
0.88	High Similarity	NPC145979
0.88	High Similarity	NPC218041
0.88	High Similarity	NPC9933
0.88	High Similarity	NPC214326
0.88	High Similarity	NPC98624
0.88	High Similarity	NPC260781
0.88	High Similarity	NPC185955
0.88	High Similarity	NPC472710
0.88	High Similarity	NPC469706
0.88	High Similarity	NPC469707
0.88	High Similarity	NPC182368
0.8776	High Similarity	NPC471667
0.8776	High Similarity	NPC79429
0.8776	High Similarity	NPC217635
0.8767	High Similarity	NPC253878
0.8718	High Similarity	NPC478267
0.8707	High Similarity	NPC185307
0.8707	High Similarity	NPC470950
0.8699	High Similarity	NPC471414
0.8684	High Similarity	NPC474442
0.8684	High Similarity	NPC21902
0.8681	High Similarity	NPC68292
0.8675	High Similarity	NPC24425
0.8658	High Similarity	NPC199928
0.8649	High Similarity	NPC129417
0.8649	High Similarity	NPC470235
0.8649	High Similarity	NPC232228
0.8649	High Similarity	NPC283995
0.8639	High Similarity	NPC131971
0.8639	High Similarity	NPC476356
0.8627	High Similarity	NPC61604
0.8627	High Similarity	NPC245615
0.8627	High Similarity	NPC115466
0.8627	High Similarity	NPC299706
0.8621	High Similarity	NPC470413
0.8621	High Similarity	NPC138738
0.8591	High Similarity	NPC163898
0.8591	High Similarity	NPC475096
0.8591	High Similarity	NPC22150
0.8591	High Similarity	NPC38041
0.8591	High Similarity	NPC279298
0.8589	High Similarity	NPC475054
0.8581	High Similarity	NPC478239
0.8581	High Similarity	NPC46092
0.8571	High Similarity	NPC472711
0.8562	High Similarity	NPC476452
0.8552	High Similarity	NPC177035
0.8552	High Similarity	NPC52277
0.8552	High Similarity	NPC199459
0.8543	High Similarity	NPC270751
0.8543	High Similarity	NPC95990
0.8533	High Similarity	NPC190714
0.8533	High Similarity	NPC112861
0.8533	High Similarity	NPC99515
0.8523	High Similarity	NPC292443
0.8514	High Similarity	NPC140502
0.8514	High Similarity	NPC472714
0.8514	High Similarity	NPC60249
0.8514	High Similarity	NPC157816
0.8514	High Similarity	NPC5262
0.8514	High Similarity	NPC48309
0.8506	High Similarity	NPC469699
0.8506	High Similarity	NPC150442
0.8503	High Similarity	NPC106944
0.8493	Intermediate Similarity	NPC304152
0.8487	Intermediate Similarity	NPC106138
0.8477	Intermediate Similarity	NPC227902
0.8477	Intermediate Similarity	NPC39657
0.8477	Intermediate Similarity	NPC474397
0.8472	Intermediate Similarity	NPC227719
0.8471	Intermediate Similarity	NPC241600
0.8471	Intermediate Similarity	NPC173726
0.8467	Intermediate Similarity	NPC161700
0.8467	Intermediate Similarity	NPC34927
0.8467	Intermediate Similarity	NPC277867
0.8467	Intermediate Similarity	NPC252292
0.8467	Intermediate Similarity	NPC18979
0.8467	Intermediate Similarity	NPC34587
0.8467	Intermediate Similarity	NPC100998
0.8467	Intermediate Similarity	NPC476382
0.8462	Intermediate Similarity	NPC163635
0.8462	Intermediate Similarity	NPC11411
0.8456	Intermediate Similarity	NPC477898
0.8456	Intermediate Similarity	NPC113680
0.8456	Intermediate Similarity	NPC278961
0.8447	Intermediate Similarity	NPC208818
0.8446	Intermediate Similarity	NPC76871
0.8446	Intermediate Similarity	NPC265075
0.8446	Intermediate Similarity	NPC186406
0.8442	Intermediate Similarity	NPC53587
0.8442	Intermediate Similarity	NPC176186
0.8442	Intermediate Similarity	NPC478268
0.8442	Intermediate Similarity	NPC169404
0.8442	Intermediate Similarity	NPC471154
0.8438	Intermediate Similarity	NPC222531
0.8435	Intermediate Similarity	NPC100389
0.8431	Intermediate Similarity	NPC158635
0.8431	Intermediate Similarity	NPC229882
0.8425	Intermediate Similarity	NPC54743
0.8425	Intermediate Similarity	NPC156502
0.8425	Intermediate Similarity	NPC477939
0.8425	Intermediate Similarity	NPC209985
0.8425	Intermediate Similarity	NPC10737
0.8425	Intermediate Similarity	NPC177160
0.8425	Intermediate Similarity	NPC29799
0.8425	Intermediate Similarity	NPC263367
0.8421	Intermediate Similarity	NPC248132
0.8421	Intermediate Similarity	NPC130449
0.8421	Intermediate Similarity	NPC175976
0.8414	Intermediate Similarity	NPC478085
0.8414	Intermediate Similarity	NPC35731
0.8414	Intermediate Similarity	NPC187194
0.8414	Intermediate Similarity	NPC476411
0.8411	Intermediate Similarity	NPC474054
0.8411	Intermediate Similarity	NPC233980
0.8411	Intermediate Similarity	NPC476865
0.8411	Intermediate Similarity	NPC125755
0.8411	Intermediate Similarity	NPC471608
0.84	Intermediate Similarity	NPC118385
0.84	Intermediate Similarity	NPC187774
0.84	Intermediate Similarity	NPC84181
0.84	Intermediate Similarity	NPC473108
0.84	Intermediate Similarity	NPC473045
0.84	Intermediate Similarity	NPC473845
0.84	Intermediate Similarity	NPC25292
0.84	Intermediate Similarity	NPC472713
0.84	Intermediate Similarity	NPC473046
0.84	Intermediate Similarity	NPC50250
0.84	Intermediate Similarity	NPC472712
0.8389	Intermediate Similarity	NPC469559
0.8389	Intermediate Similarity	NPC189115
0.8389	Intermediate Similarity	NPC246947
0.8389	Intermediate Similarity	NPC475084
0.8387	Intermediate Similarity	NPC474606
0.8387	Intermediate Similarity	NPC78809
0.8378	Intermediate Similarity	NPC202700
0.8377	Intermediate Similarity	NPC475756
0.8377	Intermediate Similarity	NPC2745
0.8375	Intermediate Similarity	NPC14294
0.8375	Intermediate Similarity	NPC116759
0.8367	Intermediate Similarity	NPC126206
0.8366	Intermediate Similarity	NPC286235
0.8366	Intermediate Similarity	NPC55158
0.8366	Intermediate Similarity	NPC51328
0.8356	Intermediate Similarity	NPC101624
0.8356	Intermediate Similarity	NPC184938
0.8356	Intermediate Similarity	NPC79957
0.8355	Intermediate Similarity	NPC232992
0.8344	Intermediate Similarity	NPC476868
0.8344	Intermediate Similarity	NPC478055
0.8344	Intermediate Similarity	NPC476866
0.8344	Intermediate Similarity	NPC307466
0.8344	Intermediate Similarity	NPC476864
0.8344	Intermediate Similarity	NPC476869
0.8333	Intermediate Similarity	NPC185498
0.8333	Intermediate Similarity	NPC265154
0.8333	Intermediate Similarity	NPC37793
0.8333	Intermediate Similarity	NPC65942
0.8333	Intermediate Similarity	NPC473044
0.8333	Intermediate Similarity	NPC312341

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 NPC159697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	880
0.2-0.3	1828
0.3-0.4	2758
0.4-0.5	1783
0.5-0.6	991
0.6-0.7	540
0.7-0.8	103
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9225	High Similarity	NPD6674	Discontinued
0.8333	Intermediate Similarity	NPD7228	Approved
0.8239	Intermediate Similarity	NPD6234	Discontinued
0.8153	Intermediate Similarity	NPD37	Approved
0.8151	Intermediate Similarity	NPD4060	Phase 1
0.8129	Intermediate Similarity	NPD1653	Approved
0.8113	Intermediate Similarity	NPD4967	Phase 2
0.8113	Intermediate Similarity	NPD4965	Approved
0.8113	Intermediate Similarity	NPD4966	Approved
0.8067	Intermediate Similarity	NPD7266	Discontinued
0.7905	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1613	Approved
0.7843	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5762	Approved
0.7829	Intermediate Similarity	NPD5763	Approved
0.7811	Intermediate Similarity	NPD7240	Approved
0.7805	Intermediate Similarity	NPD7199	Phase 2
0.7785	Intermediate Similarity	NPD3620	Phase 2
0.7785	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
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
0.7703	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD7074	Phase 3
0.7687	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7985	Registered
0.7639	Intermediate Similarity	NPD1091	Approved
0.7639	Intermediate Similarity	NPD3705	Approved
0.7635	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7054	Approved
0.7605	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7472	Approved
0.755	Intermediate Similarity	NPD4140	Approved
0.7533	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3818	Discontinued
0.7467	Intermediate Similarity	NPD4625	Phase 3
0.7459	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2861	Phase 2
0.7439	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5691	Approved
0.7417	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7473	Discontinued
0.7399	Intermediate Similarity	NPD7685	Pre-registration
0.7399	Intermediate Similarity	NPD7251	Discontinued
0.7386	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5124	Phase 1
0.7386	Intermediate Similarity	NPD5735	Approved
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7381	Intermediate Similarity	NPD8127	Discontinued
0.7379	Intermediate Similarity	NPD5125	Phase 3
0.7379	Intermediate Similarity	NPD5126	Approved
0.7378	Intermediate Similarity	NPD1934	Approved
0.7371	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7808	Phase 3
0.7343	Intermediate Similarity	NPD7340	Approved
0.7342	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4110	Phase 3
0.7342	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6797	Phase 2
0.7337	Intermediate Similarity	NPD6232	Discontinued
0.7321	Intermediate Similarity	NPD4666	Phase 3
0.7318	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4749	Approved
0.7297	Intermediate Similarity	NPD7680	Approved
0.7292	Intermediate Similarity	NPD7644	Approved
0.7285	Intermediate Similarity	NPD4908	Phase 1
0.7279	Intermediate Similarity	NPD1611	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5709	Phase 3
0.725	Intermediate Similarity	NPD5058	Phase 3
0.7248	Intermediate Similarity	NPD8651	Approved
0.7248	Intermediate Similarity	NPD6696	Suspended
0.7244	Intermediate Similarity	NPD4108	Discontinued
0.7237	Intermediate Similarity	NPD7095	Approved
0.7233	Intermediate Similarity	NPD4628	Phase 3
0.7229	Intermediate Similarity	NPD1465	Phase 2
0.7226	Intermediate Similarity	NPD6653	Approved
0.7225	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD2438	Suspended
0.7197	Intermediate Similarity	NPD6099	Approved
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7192	Intermediate Similarity	NPD1357	Approved
0.719	Intermediate Similarity	NPD6798	Discontinued
0.719	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7151	Intermediate Similarity	NPD2489	Approved
0.7151	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6843	Phase 3
0.7151	Intermediate Similarity	NPD6842	Approved
0.7151	Intermediate Similarity	NPD27	Approved
0.7151	Intermediate Similarity	NPD6166	Phase 2
0.7151	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6841	Approved
0.7133	Intermediate Similarity	NPD1283	Approved
0.7133	Intermediate Similarity	NPD1398	Phase 1
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7126	Intermediate Similarity	NPD7819	Suspended
0.7125	Intermediate Similarity	NPD8166	Discontinued
0.7119	Intermediate Similarity	NPD7311	Approved
0.7119	Intermediate Similarity	NPD7310	Approved
0.7119	Intermediate Similarity	NPD7313	Approved
0.7119	Intermediate Similarity	NPD7312	Approved
0.7117	Intermediate Similarity	NPD2675	Approved
0.7117	Intermediate Similarity	NPD2676	Approved
0.7113	Intermediate Similarity	NPD228	Approved
0.7101	Intermediate Similarity	NPD7075	Discontinued
0.7097	Intermediate Similarity	NPD2979	Phase 3
0.7093	Intermediate Similarity	NPD2969	Approved
0.7093	Intermediate Similarity	NPD2970	Approved
0.7079	Intermediate Similarity	NPD7309	Approved
0.707	Intermediate Similarity	NPD4538	Approved
0.707	Intermediate Similarity	NPD4536	Approved
0.707	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5327	Phase 3
0.7067	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1652	Phase 2
0.7055	Intermediate Similarity	NPD2532	Approved
0.7055	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD2533	Approved
0.7052	Intermediate Similarity	NPD4481	Phase 3
0.7045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6666	Approved
0.7037	Intermediate Similarity	NPD6667	Approved
0.7035	Intermediate Similarity	NPD3051	Approved
0.7035	Intermediate Similarity	NPD3787	Discontinued
0.7034	Intermediate Similarity	NPD7157	Approved
0.7034	Intermediate Similarity	NPD6671	Approved
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.7027	Intermediate Similarity	NPD1778	Approved
0.7024	Intermediate Similarity	NPD2801	Approved
0.7024	Intermediate Similarity	NPD5929	Approved
0.7024	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4663	Approved
0.7	Intermediate Similarity	NPD2424	Discontinued
0.6993	Remote Similarity	NPD5736	Approved
0.6982	Remote Similarity	NPD3817	Phase 2
0.698	Remote Similarity	NPD3496	Discontinued
0.6977	Remote Similarity	NPD6959	Discontinued
0.6975	Remote Similarity	NPD2677	Approved
0.6974	Remote Similarity	NPD3094	Phase 2
0.6968	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7906	Approved
0.6951	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7028	Phase 2
0.6944	Remote Similarity	NPD7843	Approved
0.6943	Remote Similarity	NPD3657	Discovery
0.6943	Remote Similarity	NPD7783	Phase 2
0.6943	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7229	Phase 3
0.6933	Remote Similarity	NPD1281	Approved
0.6931	Remote Similarity	NPD7435	Discontinued
0.6928	Remote Similarity	NPD3686	Approved
0.6928	Remote Similarity	NPD3687	Approved
0.6927	Remote Similarity	NPD4578	Approved
0.6927	Remote Similarity	NPD8151	Discontinued
0.6927	Remote Similarity	NPD4577	Approved
0.6923	Remote Similarity	NPD8032	Phase 2
0.6919	Remote Similarity	NPD5494	Approved
0.6918	Remote Similarity	NPD7033	Discontinued
0.6918	Remote Similarity	NPD5960	Phase 3
0.6918	Remote Similarity	NPD5588	Approved
0.6914	Remote Similarity	NPD6331	Phase 2
0.6909	Remote Similarity	NPD6273	Approved
0.6901	Remote Similarity	NPD2684	Approved
0.6899	Remote Similarity	NPD6353	Approved
0.6899	Remote Similarity	NPD4097	Suspended
0.689	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7041	Phase 2
0.6886	Remote Similarity	NPD3226	Approved
0.6875	Remote Similarity	NPD3751	Discontinued
0.6875	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD4476	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