NPASS Compound

Structure

NPC469491 OpenBabel07101719522D 26 27 0 0 1 0 0 0 0 0999 V2000 -1.7321 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.8660 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 -1.7321 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 11 2 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 1 0 0 0 21 22 1 6 0 0 0 22 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	393.934
LogP:	3.003
LogD:	2.947
LogS:	-3.877
# Rotatable Bonds:	6
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	4.788
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.297
MDCK Permeability:	1.7172525986097753e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.252

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.931
Plasma Protein Binding (PPB):	80.62553405761719%
Volume Distribution (VD):	0.881
Pgp-substrate:	11.659201622009277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.453
CYP1A2-substrate:	0.346
CYP2C19-inhibitor:	0.862
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.657
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	2.953
Half-life (T1/2):	0.064

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.679
Skin Sensitization:	0.245
Carcinogencity:	0.901
Eye Corrosion:	0.278
Eye Irritation:	0.057
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC469491

Natural Product ID:	NPC469491
*Common Name:**	Ustusolate A
IUPAC Name:	[(4S,4aS,8aS)-4-hydroxy-4-(hydroxymethyl)-4a,8,8-trimethyl-5,6,7,8a-tetrahydro-1H-naphthalen-1-yl] (2E,4E,6E)-octa-2,4,6-trienoate
Synonyms:
Standard InCHIKey:	KKQZGPSOJHPQNX-ROIWYKLJSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-5-6-7-8-9-11-18(24)26-17-12-15-22(25,16-23)21(4)14-10-13-20(2,3)19(17)21/h5-9,11-12,15,17,19,23,25H,10,13-14,16H2,1-4H3/b6-5+,8-7+,11-9+/t17?,19-,21-,22+/m0/s1
SMILES:	CC=CC=CC=CC(=O)OC1C=CC(C2(C1C(CCC2)(C)C)C)(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080770
PubChem CID:	46882364
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19769341]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	Suberites domuncula	n.a.	n.a.	PMID[19778087]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348461]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25706180]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29286660]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	30000.0	nM	PMID[565804]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	20600.0	nM	PMID[565804]

☑ 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 NPC469491 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	192
0.1-0.2	1069
0.2-0.3	3782
0.3-0.4	6839
0.4-0.5	15155
0.5-0.6	8313
0.6-0.7	5792
0.7-0.8	1468
0.8-0.85	82
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8469	Intermediate Similarity	NPC11956
0.8438	Intermediate Similarity	NPC98112
0.8427	Intermediate Similarity	NPC23748
0.8384	Intermediate Similarity	NPC23584
0.8365	Intermediate Similarity	NPC469463
0.8365	Intermediate Similarity	NPC469454
0.8365	Intermediate Similarity	NPC469496
0.8351	Intermediate Similarity	NPC65700
0.8333	Intermediate Similarity	NPC473153
0.8333	Intermediate Similarity	NPC57664
0.8315	Intermediate Similarity	NPC224455
0.828	Intermediate Similarity	NPC246028
0.8269	Intermediate Similarity	NPC470025
0.8269	Intermediate Similarity	NPC321272
0.8269	Intermediate Similarity	NPC317460
0.8269	Intermediate Similarity	NPC328074
0.8265	Intermediate Similarity	NPC38855
0.8261	Intermediate Similarity	NPC199382
0.8252	Intermediate Similarity	NPC316708
0.8252	Intermediate Similarity	NPC181298
0.8247	Intermediate Similarity	NPC205143
0.8235	Intermediate Similarity	NPC470024
0.8222	Intermediate Similarity	NPC49208
0.8218	Intermediate Similarity	NPC172867
0.8211	Intermediate Similarity	NPC53555
0.8191	Intermediate Similarity	NPC3952
0.8191	Intermediate Similarity	NPC182136
0.8191	Intermediate Similarity	NPC220216
0.819	Intermediate Similarity	NPC470027
0.8182	Intermediate Similarity	NPC472554
0.8173	Intermediate Similarity	NPC304180
0.8173	Intermediate Similarity	NPC470026
0.8173	Intermediate Similarity	NPC179798
0.8173	Intermediate Similarity	NPC17791
0.8172	Intermediate Similarity	NPC291665
0.8163	Intermediate Similarity	NPC475653
0.8155	Intermediate Similarity	NPC475274
0.8152	Intermediate Similarity	NPC61527
0.8152	Intermediate Similarity	NPC471219
0.8152	Intermediate Similarity	NPC311163
0.8137	Intermediate Similarity	NPC469959
0.8137	Intermediate Similarity	NPC108682
0.8137	Intermediate Similarity	NPC109376
0.8137	Intermediate Similarity	NPC469957
0.8137	Intermediate Similarity	NPC472263
0.8132	Intermediate Similarity	NPC83702
0.8132	Intermediate Similarity	NPC102048
0.8125	Intermediate Similarity	NPC105490
0.8125	Intermediate Similarity	NPC472360
0.8125	Intermediate Similarity	NPC472416
0.8119	Intermediate Similarity	NPC200861
0.8105	Intermediate Similarity	NPC124374
0.81	Intermediate Similarity	NPC472552
0.8095	Intermediate Similarity	NPC236217
0.8085	Intermediate Similarity	NPC20946
0.8085	Intermediate Similarity	NPC133450
0.8085	Intermediate Similarity	NPC261320
0.8085	Intermediate Similarity	NPC82876
0.8085	Intermediate Similarity	NPC16265
0.8077	Intermediate Similarity	NPC5103
0.8065	Intermediate Similarity	NPC471796
0.8065	Intermediate Similarity	NPC313658
0.8065	Intermediate Similarity	NPC316138
0.8061	Intermediate Similarity	NPC309503
0.8061	Intermediate Similarity	NPC155319
0.8061	Intermediate Similarity	NPC120299
0.8061	Intermediate Similarity	NPC125551
0.8061	Intermediate Similarity	NPC239547
0.8061	Intermediate Similarity	NPC96597
0.8061	Intermediate Similarity	NPC473244
0.8061	Intermediate Similarity	NPC91197
0.8061	Intermediate Similarity	NPC99726
0.8061	Intermediate Similarity	NPC120446
0.8058	Intermediate Similarity	NPC50124
0.8058	Intermediate Similarity	NPC224660
0.8043	Intermediate Similarity	NPC471494
0.8043	Intermediate Similarity	NPC109528
0.8041	Intermediate Similarity	NPC276110
0.8041	Intermediate Similarity	NPC300710
0.8041	Intermediate Similarity	NPC272050
0.8039	Intermediate Similarity	NPC93026
0.8039	Intermediate Similarity	NPC265502
0.8039	Intermediate Similarity	NPC469960
0.8039	Intermediate Similarity	NPC29389
0.8022	Intermediate Similarity	NPC474809
0.8021	Intermediate Similarity	NPC205034
0.8021	Intermediate Similarity	NPC162615
0.8021	Intermediate Similarity	NPC152778
0.8021	Intermediate Similarity	NPC7349
0.8021	Intermediate Similarity	NPC99653
0.802	Intermediate Similarity	NPC99266
0.8019	Intermediate Similarity	NPC56448
0.8	Intermediate Similarity	NPC71680
0.8	Intermediate Similarity	NPC11974
0.8	Intermediate Similarity	NPC8538
0.8	Intermediate Similarity	NPC184208
0.8	Intermediate Similarity	NPC177668
0.8	Intermediate Similarity	NPC315731
0.8	Intermediate Similarity	NPC310479
0.7981	Intermediate Similarity	NPC475586
0.798	Intermediate Similarity	NPC278673
0.7978	Intermediate Similarity	NPC242767
0.7978	Intermediate Similarity	NPC139712
0.7963	Intermediate Similarity	NPC23046
0.7959	Intermediate Similarity	NPC284194
0.7959	Intermediate Similarity	NPC471765
0.7959	Intermediate Similarity	NPC255410
0.7959	Intermediate Similarity	NPC165632
0.7959	Intermediate Similarity	NPC211810
0.7959	Intermediate Similarity	NPC221801
0.7959	Intermediate Similarity	NPC16967
0.7941	Intermediate Similarity	NPC146731
0.7941	Intermediate Similarity	NPC296950
0.7938	Intermediate Similarity	NPC470255
0.7938	Intermediate Similarity	NPC57117
0.7935	Intermediate Similarity	NPC160517
0.7935	Intermediate Similarity	NPC78673
0.7935	Intermediate Similarity	NPC186155
0.7935	Intermediate Similarity	NPC302360
0.7921	Intermediate Similarity	NPC137430
0.7921	Intermediate Similarity	NPC469606
0.7921	Intermediate Similarity	NPC273005
0.7921	Intermediate Similarity	NPC31058
0.7921	Intermediate Similarity	NPC473596
0.7921	Intermediate Similarity	NPC475038
0.7921	Intermediate Similarity	NPC109195
0.7917	Intermediate Similarity	NPC303697
0.7917	Intermediate Similarity	NPC234335
0.7917	Intermediate Similarity	NPC477574
0.7905	Intermediate Similarity	NPC177047
0.7905	Intermediate Similarity	NPC15551
0.79	Intermediate Similarity	NPC324841
0.79	Intermediate Similarity	NPC227865
0.7895	Intermediate Similarity	NPC314727
0.7895	Intermediate Similarity	NPC115607
0.7885	Intermediate Similarity	NPC311223
0.7885	Intermediate Similarity	NPC151393
0.7885	Intermediate Similarity	NPC475263
0.7885	Intermediate Similarity	NPC38948
0.7879	Intermediate Similarity	NPC287668
0.7879	Intermediate Similarity	NPC475332
0.7872	Intermediate Similarity	NPC131329
0.7872	Intermediate Similarity	NPC471779
0.7872	Intermediate Similarity	NPC245004
0.7864	Intermediate Similarity	NPC218158
0.7864	Intermediate Similarity	NPC477125
0.7864	Intermediate Similarity	NPC471206
0.7864	Intermediate Similarity	NPC82251
0.7864	Intermediate Similarity	NPC88349
0.7849	Intermediate Similarity	NPC471795
0.7849	Intermediate Similarity	NPC11804
0.7849	Intermediate Similarity	NPC35933
0.7843	Intermediate Similarity	NPC183570
0.7843	Intermediate Similarity	NPC134270
0.7843	Intermediate Similarity	NPC8196
0.7843	Intermediate Similarity	NPC45897
0.7835	Intermediate Similarity	NPC476049
0.783	Intermediate Similarity	NPC284162
0.783	Intermediate Similarity	NPC255401
0.783	Intermediate Similarity	NPC324683
0.783	Intermediate Similarity	NPC471484
0.783	Intermediate Similarity	NPC470076
0.783	Intermediate Similarity	NPC262083
0.7826	Intermediate Similarity	NPC311070
0.7826	Intermediate Similarity	NPC57370
0.7822	Intermediate Similarity	NPC280991
0.7822	Intermediate Similarity	NPC169365
0.7822	Intermediate Similarity	NPC97435
0.7822	Intermediate Similarity	NPC475617
0.7822	Intermediate Similarity	NPC197447
0.7812	Intermediate Similarity	NPC48732
0.7812	Intermediate Similarity	NPC221111
0.7812	Intermediate Similarity	NPC78973
0.7812	Intermediate Similarity	NPC280149
0.7812	Intermediate Similarity	NPC473448
0.781	Intermediate Similarity	NPC206618
0.781	Intermediate Similarity	NPC316974
0.781	Intermediate Similarity	NPC137911
0.781	Intermediate Similarity	NPC228477
0.78	Intermediate Similarity	NPC218107
0.78	Intermediate Similarity	NPC475068
0.78	Intermediate Similarity	NPC23364
0.78	Intermediate Similarity	NPC222303
0.78	Intermediate Similarity	NPC316598
0.7789	Intermediate Similarity	NPC7280
0.7789	Intermediate Similarity	NPC229612
0.7788	Intermediate Similarity	NPC88013
0.7788	Intermediate Similarity	NPC67321
0.7788	Intermediate Similarity	NPC187435
0.7788	Intermediate Similarity	NPC473586
0.7788	Intermediate Similarity	NPC125423
0.7778	Intermediate Similarity	NPC190713
0.7778	Intermediate Similarity	NPC202833
0.7778	Intermediate Similarity	NPC216665
0.7778	Intermediate Similarity	NPC305044
0.7778	Intermediate Similarity	NPC472995
0.7778	Intermediate Similarity	NPC265290
0.7778	Intermediate Similarity	NPC86971
0.7778	Intermediate Similarity	NPC129569
0.7767	Intermediate Similarity	NPC272632

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 NPC469491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1284
0.2-0.3	3509
0.3-0.4	2595
0.4-0.5	1116
0.5-0.6	317
0.6-0.7	150
0.7-0.8	12
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
0.8	Intermediate Similarity	NPD7838	Discovery
0.8	Intermediate Similarity	NPD5344	Discontinued
0.79	Intermediate Similarity	NPD6648	Approved
0.78	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD4225	Approved
0.7549	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD7639	Approved
0.7547	Intermediate Similarity	NPD6686	Approved
0.7522	Intermediate Similarity	NPD7503	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.7374	Intermediate Similarity	NPD7637	Suspended
0.7368	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7524	Approved
0.73	Intermediate Similarity	NPD5779	Approved
0.73	Intermediate Similarity	NPD5778	Approved
0.7273	Intermediate Similarity	NPD46	Approved
0.7273	Intermediate Similarity	NPD6698	Approved
0.7263	Intermediate Similarity	NPD6695	Phase 3
0.7188	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7091	Intermediate Similarity	NPD6371	Approved
0.703	Intermediate Similarity	NPD7983	Approved
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7750	Discontinued
0.6957	Remote Similarity	NPD8264	Approved
0.6957	Remote Similarity	NPD7327	Approved
0.6957	Remote Similarity	NPD7328	Approved
0.6947	Remote Similarity	NPD6931	Approved
0.6947	Remote Similarity	NPD7332	Phase 2
0.6947	Remote Similarity	NPD6930	Phase 2
0.6947	Remote Similarity	NPD7514	Phase 3
0.6931	Remote Similarity	NPD5785	Approved
0.6923	Remote Similarity	NPD8033	Approved
0.6916	Remote Similarity	NPD7632	Discontinued
0.6897	Remote Similarity	NPD7516	Approved
0.6882	Remote Similarity	NPD6933	Approved
0.6863	Remote Similarity	NPD6411	Approved
0.6842	Remote Similarity	NPD6929	Approved
0.6838	Remote Similarity	NPD8294	Approved
0.6838	Remote Similarity	NPD8377	Approved
0.6832	Remote Similarity	NPD6051	Approved
0.6814	Remote Similarity	NPD6053	Discontinued
0.678	Remote Similarity	NPD8335	Approved
0.678	Remote Similarity	NPD8296	Approved
0.678	Remote Similarity	NPD8378	Approved
0.678	Remote Similarity	NPD8380	Approved
0.678	Remote Similarity	NPD8379	Approved
0.6754	Remote Similarity	NPD4632	Approved
0.6737	Remote Similarity	NPD7145	Approved
0.6737	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6902	Approved
0.6699	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6399	Phase 3
0.6634	Remote Similarity	NPD4250	Approved
0.6634	Remote Similarity	NPD4251	Approved
0.6632	Remote Similarity	NPD6925	Approved
0.6632	Remote Similarity	NPD5776	Phase 2
0.6632	Remote Similarity	NPD6932	Approved
0.6607	Remote Similarity	NPD6881	Approved
0.6607	Remote Similarity	NPD6899	Approved
0.6607	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6893	Approved
0.66	Remote Similarity	NPD1694	Approved
0.6598	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4822	Approved
0.6598	Remote Similarity	NPD4819	Approved
0.6598	Remote Similarity	NPD4821	Approved
0.6598	Remote Similarity	NPD4820	Approved
0.6596	Remote Similarity	NPD8039	Approved
0.6591	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7748	Approved
0.656	Remote Similarity	NPD7260	Phase 2
0.6557	Remote Similarity	NPD7507	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6542	Remote Similarity	NPD7902	Approved
0.6542	Remote Similarity	NPD6083	Phase 2
0.6542	Remote Similarity	NPD6084	Phase 2
0.6538	Remote Similarity	NPD5284	Approved
0.6538	Remote Similarity	NPD7515	Phase 2
0.6538	Remote Similarity	NPD5281	Approved
0.6535	Remote Similarity	NPD4249	Approved
0.6531	Remote Similarity	NPD6898	Phase 1
0.6522	Remote Similarity	NPD8297	Approved
0.6518	Remote Similarity	NPD5697	Approved
0.6509	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8513	Phase 3
0.65	Remote Similarity	NPD8515	Approved
0.65	Remote Similarity	NPD8517	Approved
0.65	Remote Similarity	NPD8516	Approved
0.6491	Remote Similarity	NPD7102	Approved
0.6491	Remote Similarity	NPD6883	Approved
0.6491	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5209	Approved
0.646	Remote Similarity	NPD6011	Approved
0.6441	Remote Similarity	NPD6009	Approved
0.6436	Remote Similarity	NPD5363	Approved
0.6435	Remote Similarity	NPD6617	Approved
0.6435	Remote Similarity	NPD6869	Approved
0.6435	Remote Similarity	NPD6650	Approved
0.6435	Remote Similarity	NPD6649	Approved
0.6435	Remote Similarity	NPD6847	Approved
0.6435	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD7509	Discontinued
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6429	Remote Similarity	NPD6640	Phase 3
0.6404	Remote Similarity	NPD6012	Approved
0.6404	Remote Similarity	NPD6014	Approved
0.6404	Remote Similarity	NPD6013	Approved
0.64	Remote Similarity	NPD7319	Approved
0.6393	Remote Similarity	NPD7604	Phase 2
0.6392	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4268	Approved
0.6392	Remote Similarity	NPD4271	Approved
0.6379	Remote Similarity	NPD6882	Approved
0.6373	Remote Similarity	NPD5279	Phase 3
0.6373	Remote Similarity	NPD7334	Approved
0.6373	Remote Similarity	NPD6409	Approved
0.6373	Remote Similarity	NPD7146	Approved
0.6373	Remote Similarity	NPD5330	Approved
0.6373	Remote Similarity	NPD7521	Approved
0.6373	Remote Similarity	NPD6684	Approved
0.6372	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4192	Approved
0.6364	Remote Similarity	NPD4194	Approved
0.6364	Remote Similarity	NPD5983	Phase 2
0.6364	Remote Similarity	NPD4193	Approved
0.6364	Remote Similarity	NPD4191	Approved
0.6355	Remote Similarity	NPD5695	Phase 3
0.6346	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7144	Approved
0.6344	Remote Similarity	NPD7143	Approved
0.6341	Remote Similarity	NPD7492	Approved
0.6333	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4195	Approved
0.6327	Remote Similarity	NPD6683	Phase 2
0.6316	Remote Similarity	NPD7320	Approved
0.6306	Remote Similarity	NPD5211	Phase 2
0.6296	Remote Similarity	NPD7839	Suspended
0.629	Remote Similarity	NPD6336	Discontinued
0.629	Remote Similarity	NPD6616	Approved
0.6283	Remote Similarity	NPD6008	Approved
0.6281	Remote Similarity	NPD6054	Approved
0.6277	Remote Similarity	NPD7152	Approved
0.6277	Remote Similarity	NPD7150	Approved
0.6277	Remote Similarity	NPD7151	Approved
0.6275	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1696	Phase 3
0.6263	Remote Similarity	NPD4695	Discontinued
0.6263	Remote Similarity	NPD7525	Registered
0.6263	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5282	Discontinued
0.6262	Remote Similarity	NPD7900	Approved
0.6262	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6373	Approved
0.6261	Remote Similarity	NPD6372	Approved
0.626	Remote Similarity	NPD7829	Approved
0.626	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6942	Approved
0.625	Remote Similarity	NPD6672	Approved
0.625	Remote Similarity	NPD6903	Approved
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.624	Remote Similarity	NPD8074	Phase 3
0.624	Remote Similarity	NPD7078	Approved
0.6238	Remote Similarity	NPD5362	Discontinued
0.6238	Remote Similarity	NPD7154	Phase 3
0.6238	Remote Similarity	NPD6110	Phase 1
0.6237	Remote Similarity	NPD6923	Approved
0.6237	Remote Similarity	NPD6922	Approved
0.6228	Remote Similarity	NPD5701	Approved
0.6226	Remote Similarity	NPD6079	Approved
0.6226	Remote Similarity	NPD5693	Phase 1
0.6226	Remote Similarity	NPD6050	Approved
0.6226	Remote Similarity	NPD5694	Approved
0.6214	Remote Similarity	NPD4623	Approved
0.6214	Remote Similarity	NPD4519	Discontinued
0.6211	Remote Similarity	NPD4732	Discontinued
0.6207	Remote Similarity	NPD4634	Approved
0.6195	Remote Similarity	NPD5141	Approved
0.619	Remote Similarity	NPD7736	Approved
0.6186	Remote Similarity	NPD8133	Approved
0.6186	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5696	Approved
0.6179	Remote Similarity	NPD6370	Approved
0.6176	Remote Similarity	NPD3666	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