NPASS Compound

Structure

NPC475878 OpenBabel07101719142D 30 34 0 0 1 0 0 0 0 0999 V2000 -2.4122 -3.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2455 -1.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2455 -1.6589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0124 1.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5461 -3.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4786 0.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5461 -2.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8296 2.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4054 1.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4786 -0.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7455 0.9002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2793 -0.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9855 2.2945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2793 0.9002 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.0124 -0.3696 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5461 -0.3696 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6801 -1.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9705 1.2946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0392 2.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9463 -0.3232 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7455 -0.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0124 0.4769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5461 0.4769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1859 -2.3696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2556 3.5733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2411 -1.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6801 -0.8696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5607 1.8176 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 1 5 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 9 14 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 8 1 1 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 23 1 0 0 0 0 14 24 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 1 0 0 0 16 24 1 6 0 0 0 16 28 1 0 0 0 0 17 25 2 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 1 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 20 29 1 1 0 0 0 20 30 1 0 0 0 0 21 24 1 1 0 0 0 21 27 1 0 0 0 0 21 30 1 0 0 0 0 23 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.25
Volume:	428.346
LogP:	4.183
LogD:	3.418
LogS:	-4.641
# Rotatable Bonds:	4
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	5.508
Fsp3:	0.917
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.835
MDCK Permeability:	5.054676876170561e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.893

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.349
Plasma Protein Binding (PPB):	86.14592742919922%
Volume Distribution (VD):	1.669
Pgp-substrate:	16.627521514892578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.311
CYP2C9-substrate:	0.103
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.487
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	9.372
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.485
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.362
Maximum Recommended Daily Dose:	0.385
Skin Sensitization:	0.194
Carcinogencity:	0.148
Eye Corrosion:	0.023
Eye Irritation:	0.019
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC475878

Natural Product ID:	NPC475878
*Common Name:**	Aplyroseol 1
IUPAC Name:	n.a.
Synonyms:	Aplyroseol 1
Standard InCHIKey:	VDGDSNQYFYXHGB-UMHJJXCQSA-N
Standard InCHI:	InChI=1S/C24H36O6/c1-5-7-17(25)28-16-12-15-22(2,3)10-6-11-23(15,4)14-9-8-13-18-20(29-19(13)26)30-21(27)24(14,16)18/h13-16,18,20-21,27H,5-12H2,1-4H3/t13-,14?,15+,16-,18+,20+,21-,23-,24-/m1/s1
SMILES:	CCCC(=O)O[C@@H]1C[C@H]2C(C)(C)CCC[C@@]2(C2[C@]31[C@H](O)O[C@H]1[C@@H]3[C@@H](CC2)C(=O)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517823
PubChem CID:	44584708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001816] Furofurans

*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
NPO24090	Aplysilla rosea	Species	Darwinellidae	Eukaryota	n.a.	Austrila	n.a.	Database[Title]
NPO24090	Aplysilla rosea	Species	Darwinellidae	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
Others	1

Activity Type	# Activity
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24397	SINGLE PROTEIN	Phospholipase A2	Apis mellifera	Activity	=	65.0	%	PMID[523795]

☑ 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 NPC475878 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	402
0.1-0.2	3235
0.2-0.3	8460
0.3-0.4	13811
0.4-0.5	6278
0.5-0.6	4923
0.6-0.7	4322
0.7-0.8	1122
0.8-0.85	114
0.85-0.9	14
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9551	High Similarity	NPC475785
0.9551	High Similarity	NPC475765
0.8817	High Similarity	NPC472145
0.8736	High Similarity	NPC473299
0.8723	High Similarity	NPC472144
0.871	High Similarity	NPC193785
0.8646	High Similarity	NPC244969
0.8646	High Similarity	NPC213528
0.8621	High Similarity	NPC474284
0.8621	High Similarity	NPC474253
0.8621	High Similarity	NPC213737
0.8621	High Similarity	NPC474346
0.8621	High Similarity	NPC475820
0.8617	High Similarity	NPC472273
0.8571	High Similarity	NPC470114
0.8556	High Similarity	NPC221993
0.8506	High Similarity	NPC2096
0.8506	High Similarity	NPC208912
0.8469	Intermediate Similarity	NPC100078
0.8462	Intermediate Similarity	NPC67653
0.8462	Intermediate Similarity	NPC471459
0.8427	Intermediate Similarity	NPC235402
0.8421	Intermediate Similarity	NPC266417
0.8409	Intermediate Similarity	NPC15091
0.8387	Intermediate Similarity	NPC161035
0.8384	Intermediate Similarity	NPC306776
0.8384	Intermediate Similarity	NPC166079
0.8352	Intermediate Similarity	NPC476435
0.8352	Intermediate Similarity	NPC471221
0.8315	Intermediate Similarity	NPC477434
0.8315	Intermediate Similarity	NPC18953
0.8276	Intermediate Similarity	NPC134227
0.8229	Intermediate Similarity	NPC470632
0.8211	Intermediate Similarity	NPC305808
0.8191	Intermediate Similarity	NPC475307
0.8191	Intermediate Similarity	NPC472231
0.8191	Intermediate Similarity	NPC476189
0.8191	Intermediate Similarity	NPC472232
0.8182	Intermediate Similarity	NPC475743
0.8172	Intermediate Similarity	NPC50443
0.8172	Intermediate Similarity	NPC18536
0.8152	Intermediate Similarity	NPC470872
0.8132	Intermediate Similarity	NPC471410
0.8132	Intermediate Similarity	NPC83242
0.8132	Intermediate Similarity	NPC471411
0.8125	Intermediate Similarity	NPC235109
0.8125	Intermediate Similarity	NPC476728
0.8119	Intermediate Similarity	NPC126753
0.8119	Intermediate Similarity	NPC203974
0.8111	Intermediate Similarity	NPC219535
0.8111	Intermediate Similarity	NPC237938
0.81	Intermediate Similarity	NPC88469
0.8095	Intermediate Similarity	NPC79193
0.8085	Intermediate Similarity	NPC474065
0.8068	Intermediate Similarity	NPC125366
0.8068	Intermediate Similarity	NPC471217
0.8068	Intermediate Similarity	NPC471216
0.8068	Intermediate Similarity	NPC475456
0.8065	Intermediate Similarity	NPC61688
0.8065	Intermediate Similarity	NPC200580
0.8065	Intermediate Similarity	NPC477443
0.8065	Intermediate Similarity	NPC477440
0.8058	Intermediate Similarity	NPC470622
0.8058	Intermediate Similarity	NPC98069
0.8058	Intermediate Similarity	NPC98633
0.8058	Intermediate Similarity	NPC49730
0.8043	Intermediate Similarity	NPC213658
0.8043	Intermediate Similarity	NPC45833
0.8043	Intermediate Similarity	NPC110365
0.8043	Intermediate Similarity	NPC62202
0.8041	Intermediate Similarity	NPC471241
0.8041	Intermediate Similarity	NPC74466
0.8022	Intermediate Similarity	NPC477445
0.8022	Intermediate Similarity	NPC478111
0.8021	Intermediate Similarity	NPC82633
0.8021	Intermediate Similarity	NPC287354
0.8021	Intermediate Similarity	NPC62407
0.8021	Intermediate Similarity	NPC21897
0.802	Intermediate Similarity	NPC215408
0.8	Intermediate Similarity	NPC34562
0.7981	Intermediate Similarity	NPC471251
0.7979	Intermediate Similarity	NPC477442
0.7979	Intermediate Similarity	NPC88337
0.7979	Intermediate Similarity	NPC477444
0.7979	Intermediate Similarity	NPC477433
0.7979	Intermediate Similarity	NPC472146
0.7979	Intermediate Similarity	NPC77756
0.7979	Intermediate Similarity	NPC475211
0.7979	Intermediate Similarity	NPC185529
0.7978	Intermediate Similarity	NPC71541
0.7978	Intermediate Similarity	NPC271572
0.7978	Intermediate Similarity	NPC58631
0.7978	Intermediate Similarity	NPC474870
0.7961	Intermediate Similarity	NPC236753
0.7961	Intermediate Similarity	NPC471250
0.7961	Intermediate Similarity	NPC228190
0.7957	Intermediate Similarity	NPC236459
0.7957	Intermediate Similarity	NPC131104
0.7957	Intermediate Similarity	NPC473319
0.7957	Intermediate Similarity	NPC3032
0.7955	Intermediate Similarity	NPC80891
0.7955	Intermediate Similarity	NPC201276
0.7955	Intermediate Similarity	NPC474754
0.7941	Intermediate Similarity	NPC96333
0.7941	Intermediate Similarity	NPC88833
0.7938	Intermediate Similarity	NPC116683
0.7938	Intermediate Similarity	NPC163685
0.7935	Intermediate Similarity	NPC474008
0.7935	Intermediate Similarity	NPC248216
0.7931	Intermediate Similarity	NPC307865
0.7931	Intermediate Similarity	NPC143250
0.7917	Intermediate Similarity	NPC470424
0.7912	Intermediate Similarity	NPC79308
0.7912	Intermediate Similarity	NPC473336
0.7912	Intermediate Similarity	NPC471044
0.7912	Intermediate Similarity	NPC65133
0.7905	Intermediate Similarity	NPC157571
0.79	Intermediate Similarity	NPC80640
0.7895	Intermediate Similarity	NPC52756
0.7885	Intermediate Similarity	NPC471431
0.7879	Intermediate Similarity	NPC80417
0.7864	Intermediate Similarity	NPC475319
0.7864	Intermediate Similarity	NPC207693
0.7864	Intermediate Similarity	NPC469826
0.7864	Intermediate Similarity	NPC92890
0.7864	Intermediate Similarity	NPC202898
0.7864	Intermediate Similarity	NPC469845
0.7849	Intermediate Similarity	NPC470920
0.7849	Intermediate Similarity	NPC252714
0.7849	Intermediate Similarity	NPC239938
0.7843	Intermediate Similarity	NPC164600
0.7843	Intermediate Similarity	NPC158367
0.7843	Intermediate Similarity	NPC158051
0.7843	Intermediate Similarity	NPC103172
0.7843	Intermediate Similarity	NPC285927
0.7843	Intermediate Similarity	NPC119628
0.7841	Intermediate Similarity	NPC224802
0.7841	Intermediate Similarity	NPC34046
0.7841	Intermediate Similarity	NPC324700
0.7841	Intermediate Similarity	NPC80089
0.7841	Intermediate Similarity	NPC171426
0.7835	Intermediate Similarity	NPC215570
0.783	Intermediate Similarity	NPC285086
0.7826	Intermediate Similarity	NPC62572
0.7826	Intermediate Similarity	NPC473350
0.7822	Intermediate Similarity	NPC107385
0.7816	Intermediate Similarity	NPC474020
0.7812	Intermediate Similarity	NPC182740
0.7812	Intermediate Similarity	NPC211845
0.7812	Intermediate Similarity	NPC122083
0.7812	Intermediate Similarity	NPC256104
0.781	Intermediate Similarity	NPC469824
0.781	Intermediate Similarity	NPC329953
0.781	Intermediate Similarity	NPC473062
0.78	Intermediate Similarity	NPC178853
0.7791	Intermediate Similarity	NPC55508
0.7788	Intermediate Similarity	NPC22709
0.7788	Intermediate Similarity	NPC273002
0.7788	Intermediate Similarity	NPC92297
0.7788	Intermediate Similarity	NPC473817
0.7788	Intermediate Similarity	NPC94086
0.7788	Intermediate Similarity	NPC233433
0.7788	Intermediate Similarity	NPC220836
0.7788	Intermediate Similarity	NPC87393
0.7778	Intermediate Similarity	NPC28864
0.7778	Intermediate Similarity	NPC162459
0.7778	Intermediate Similarity	NPC38471
0.7778	Intermediate Similarity	NPC98837
0.7778	Intermediate Similarity	NPC179429
0.7778	Intermediate Similarity	NPC292775
0.7778	Intermediate Similarity	NPC280781
0.7778	Intermediate Similarity	NPC20479
0.7778	Intermediate Similarity	NPC476071
0.7778	Intermediate Similarity	NPC48756
0.7778	Intermediate Similarity	NPC38296
0.7767	Intermediate Similarity	NPC475630
0.7767	Intermediate Similarity	NPC138219
0.7767	Intermediate Similarity	NPC61071
0.7767	Intermediate Similarity	NPC40716
0.7767	Intermediate Similarity	NPC475234
0.7766	Intermediate Similarity	NPC476379
0.7755	Intermediate Similarity	NPC238796
0.7755	Intermediate Similarity	NPC200054
0.7755	Intermediate Similarity	NPC237071
0.7755	Intermediate Similarity	NPC256227
0.7755	Intermediate Similarity	NPC29410
0.7755	Intermediate Similarity	NPC203434
0.7753	Intermediate Similarity	NPC320144
0.7745	Intermediate Similarity	NPC267637
0.7745	Intermediate Similarity	NPC469827
0.7745	Intermediate Similarity	NPC101842
0.7745	Intermediate Similarity	NPC470167
0.7742	Intermediate Similarity	NPC302111
0.7742	Intermediate Similarity	NPC80700
0.7742	Intermediate Similarity	NPC472272
0.7736	Intermediate Similarity	NPC477489
0.7727	Intermediate Similarity	NPC207010
0.7727	Intermediate Similarity	NPC317913
0.7723	Intermediate Similarity	NPC470172
0.7714	Intermediate Similarity	NPC66513

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 NPC475878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	3457
0.2-0.3	3471
0.3-0.4	1042
0.4-0.5	371
0.5-0.6	231
0.6-0.7	130
0.7-0.8	20
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7921	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6697	Approved
0.7841	Intermediate Similarity	NPD6118	Approved
0.7841	Intermediate Similarity	NPD6115	Approved
0.7841	Intermediate Similarity	NPD6114	Approved
0.7727	Intermediate Similarity	NPD6116	Phase 1
0.7614	Intermediate Similarity	NPD6117	Approved
0.75	Intermediate Similarity	NPD3703	Phase 2
0.7386	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6928	Phase 2
0.7204	Intermediate Similarity	NPD1779	Approved
0.7204	Intermediate Similarity	NPD1780	Approved
0.71	Intermediate Similarity	NPD8171	Discontinued
0.7053	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3669	Approved
0.7027	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD8035	Phase 2
0.7	Intermediate Similarity	NPD8034	Phase 2
0.6975	Remote Similarity	NPD7736	Approved
0.6966	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD1700	Approved
0.6949	Remote Similarity	NPD7507	Approved
0.6932	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8328	Phase 3
0.6903	Remote Similarity	NPD6940	Discontinued
0.6891	Remote Similarity	NPD8293	Discontinued
0.6881	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6370	Approved
0.6778	Remote Similarity	NPD5777	Approved
0.6777	Remote Similarity	NPD7319	Approved
0.6739	Remote Similarity	NPD3702	Approved
0.6735	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6686	Approved
0.6723	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6637	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6612	Remote Similarity	NPD7078	Approved
0.6606	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7638	Approved
0.6593	Remote Similarity	NPD6081	Approved
0.6591	Remote Similarity	NPD4224	Phase 2
0.6577	Remote Similarity	NPD7320	Approved
0.6556	Remote Similarity	NPD3698	Phase 2
0.6545	Remote Similarity	NPD5739	Approved
0.6545	Remote Similarity	NPD6008	Approved
0.6545	Remote Similarity	NPD6675	Approved
0.6545	Remote Similarity	NPD6402	Approved
0.6545	Remote Similarity	NPD7128	Approved
0.6542	Remote Similarity	NPD7639	Approved
0.6542	Remote Similarity	NPD7640	Approved
0.6518	Remote Similarity	NPD6372	Approved
0.6518	Remote Similarity	NPD6373	Approved
0.6509	Remote Similarity	NPD7902	Approved
0.6484	Remote Similarity	NPD4789	Approved
0.6471	Remote Similarity	NPD6016	Approved
0.6471	Remote Similarity	NPD6015	Approved
0.6452	Remote Similarity	NPD1810	Approved
0.6452	Remote Similarity	NPD1811	Approved
0.6444	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5360	Phase 3
0.6444	Remote Similarity	NPD229	Approved
0.6442	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD6899	Approved
0.6422	Remote Similarity	NPD7632	Discontinued
0.6417	Remote Similarity	NPD5988	Approved
0.641	Remote Similarity	NPD6009	Approved
0.6404	Remote Similarity	NPD6649	Approved
0.6404	Remote Similarity	NPD6650	Approved
0.6389	Remote Similarity	NPD8418	Phase 2
0.6381	Remote Similarity	NPD7748	Approved
0.6374	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6067	Discontinued
0.6356	Remote Similarity	NPD7328	Approved
0.6356	Remote Similarity	NPD7327	Approved
0.6354	Remote Similarity	NPD3671	Phase 1
0.6346	Remote Similarity	NPD7515	Phase 2
0.6339	Remote Similarity	NPD5701	Approved
0.6339	Remote Similarity	NPD5697	Approved
0.6321	Remote Similarity	NPD7991	Discontinued
0.6316	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD7290	Approved
0.6316	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6883	Approved
0.6304	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7516	Approved
0.6292	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6847	Approved
0.6261	Remote Similarity	NPD8130	Phase 1
0.6261	Remote Similarity	NPD6869	Approved
0.6261	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD8377	Approved
0.6228	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD6014	Approved
0.6228	Remote Similarity	NPD6012	Approved
0.6226	Remote Similarity	NPD7900	Approved
0.6226	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8297	Approved
0.6198	Remote Similarity	NPD8378	Approved
0.6198	Remote Similarity	NPD8513	Phase 3
0.6198	Remote Similarity	NPD8515	Approved
0.6198	Remote Similarity	NPD8033	Approved
0.6198	Remote Similarity	NPD8516	Approved
0.6198	Remote Similarity	NPD8335	Approved
0.6198	Remote Similarity	NPD8296	Approved
0.6198	Remote Similarity	NPD8517	Approved
0.6198	Remote Similarity	NPD6921	Approved
0.6198	Remote Similarity	NPD8380	Approved
0.6198	Remote Similarity	NPD8379	Approved
0.6186	Remote Similarity	NPD4802	Phase 2
0.6186	Remote Similarity	NPD4238	Approved
0.616	Remote Similarity	NPD6033	Approved
0.6154	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD4632	Approved
0.614	Remote Similarity	NPD6011	Approved
0.6129	Remote Similarity	NPD2687	Approved
0.6129	Remote Similarity	NPD2254	Approved
0.6129	Remote Similarity	NPD2686	Approved
0.6126	Remote Similarity	NPD8085	Approved
0.6126	Remote Similarity	NPD8139	Approved
0.6126	Remote Similarity	NPD8083	Approved
0.6126	Remote Similarity	NPD8084	Approved
0.6126	Remote Similarity	NPD8138	Approved
0.6126	Remote Similarity	NPD8082	Approved
0.6126	Remote Similarity	NPD8086	Approved
0.6121	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6319	Approved
0.6111	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8275	Approved
0.6071	Remote Similarity	NPD8276	Approved
0.6064	Remote Similarity	NPD4758	Discontinued
0.6055	Remote Similarity	NPD4755	Approved
0.6053	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6079	Approved
0.6038	Remote Similarity	NPD6411	Approved
0.602	Remote Similarity	NPD5364	Discontinued
0.6019	Remote Similarity	NPD3618	Phase 1
0.6018	Remote Similarity	NPD8081	Approved
0.5968	Remote Similarity	NPD7604	Phase 2
0.5965	Remote Similarity	NPD8393	Approved
0.5963	Remote Similarity	NPD4697	Phase 3
0.5946	Remote Similarity	NPD5285	Approved
0.5946	Remote Similarity	NPD5286	Approved
0.5946	Remote Similarity	NPD4696	Approved
0.5946	Remote Similarity	NPD4700	Approved
0.5935	Remote Similarity	NPD5983	Phase 2
0.5935	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6274	Approved
0.5909	Remote Similarity	NPD6084	Phase 2
0.5909	Remote Similarity	NPD6083	Phase 2
0.5902	Remote Similarity	NPD7100	Approved
0.5902	Remote Similarity	NPD7101	Approved
0.5882	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD2257	Approved
0.5873	Remote Similarity	NPD6336	Discontinued
0.5872	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4225	Approved
0.5849	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6101	Approved
0.5841	Remote Similarity	NPD5226	Approved
0.5841	Remote Similarity	NPD4633	Approved
0.5841	Remote Similarity	NPD5211	Phase 2
0.5841	Remote Similarity	NPD5225	Approved
0.5841	Remote Similarity	NPD5224	Approved
0.5833	Remote Similarity	NPD5779	Approved
0.5833	Remote Similarity	NPD5778	Approved
0.5825	Remote Similarity	NPD4786	Approved
0.5824	Remote Similarity	NPD7909	Approved
0.582	Remote Similarity	NPD6335	Approved
0.5818	Remote Similarity	NPD5221	Approved
0.5818	Remote Similarity	NPD5222	Approved
0.5818	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7503	Approved
0.5806	Remote Similarity	NPD6908	Approved
0.5806	Remote Similarity	NPD6909	Approved
0.58	Remote Similarity	NPD7329	Approved
0.5798	Remote Similarity	NPD6053	Discontinued
0.5789	Remote Similarity	NPD5175	Approved
0.5789	Remote Similarity	NPD4787	Phase 1
0.5789	Remote Similarity	NPD5174	Approved
0.5785	Remote Similarity	NPD6868	Approved
0.5784	Remote Similarity	NPD3667	Approved
0.5776	Remote Similarity	NPD8140	Approved
0.5776	Remote Similarity	NPD8307	Discontinued
0.5766	Remote Similarity	NPD5173	Approved
0.5763	Remote Similarity	NPD4634	Approved
0.5755	Remote Similarity	NPD6903	Approved
0.5755	Remote Similarity	NPD7513	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