NPASS Compound

Structure

NPC230823 OpenBabel07101718232D 21 22 0 0 1 0 0 0 0 0999 V2000 -1.9935 2.6696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3028 3.0458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1300 2.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6502 -2.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9675 0.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5094 0.1672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3201 1.1491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1377 -0.7612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6582 2.1086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7132 1.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4843 0.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9761 -0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3243 -1.3888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0395 2.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6300 1.8728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3231 -1.3413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8223 1.3935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0951 0.9955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4582 -0.8888 0.0000 C 0 0 0 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 -0.2655 -1.5789 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 3 15 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 16 4 1 1 0 0 0 17 18 1 0 0 0 0 18 20 1 1 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	5.569
LogD:	4.942
LogS:	-6.008
# Rotatable Bonds:	0
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	4.452
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.783
MDCK Permeability:	1.8806964362738654e-05
Pgp-inhibitor:	0.797
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.864

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.465
Plasma Protein Binding (PPB):	96.44850158691406%
Volume Distribution (VD):	2.92
Pgp-substrate:	2.667515277862549%

ADMET: Metabolism

CYP1A2-inhibitor:	0.23
CYP1A2-substrate:	0.521
CYP2C19-inhibitor:	0.422
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.523
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.411
CYP3A4-inhibitor:	0.43
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	7.766
Half-life (T1/2):	0.408

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.223
Drug-inuced Liver Injury (DILI):	0.189
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.505
Skin Sensitization:	0.882
Carcinogencity:	0.054
Eye Corrosion:	0.09
Eye Irritation:	0.878
Respiratory Toxicity:	0.202

Download Data

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

Natural Product: NPC230823

Natural Product ID:	NPC230823
*Common Name:**	Edunone
IUPAC Name:	(3aR,6R,9E,12aR)-3a,6,10-trimethyl-1-propan-2-ylidene-3,5,6,7,8,11,12,12a-octahydro-2H-cyclopenta[11]annulen-4-one
Synonyms:	Edunone
Standard InCHIKey:	AMAPASJFIMKPND-ILUKQUFFSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-14(2)17-11-12-20(5)18(17)10-9-15(3)7-6-8-16(4)13-19(20)21/h7,16,18H,6,8-13H2,1-5H3/b15-7+/t16-,18-,20-/m1/s1
SMILES:	CC(=C1CC[C@]2(C)[C@@H]1CC/C(=C/CC[C@@H](C)CC2=O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513539
PubChem CID:	10062670
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO22554	Eunicea laciniata	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[7769391]
NPO22554	Eunicea laciniata	Species	Plexauridae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	25.0	ug.mL-1	PMID[484911]

☑ 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 NPC230823 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	184
0.1-0.2	3013
0.2-0.3	17686
0.3-0.4	10435
0.4-0.5	7227
0.5-0.6	3302
0.6-0.7	703
0.7-0.8	121
0.8-0.85	7
0.85-0.9	9
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC55004
0.963	High Similarity	NPC267626
0.963	High Similarity	NPC49575
0.9455	High Similarity	NPC94991
0.9455	High Similarity	NPC266295
0.9286	High Similarity	NPC259261
0.9123	High Similarity	NPC25853
0.9107	High Similarity	NPC30215
0.8667	High Similarity	NPC473902
0.8644	High Similarity	NPC475795
0.85	High Similarity	NPC165695
0.8413	Intermediate Similarity	NPC20610
0.8361	Intermediate Similarity	NPC212210
0.8333	Intermediate Similarity	NPC213152
0.8333	Intermediate Similarity	NPC60565
0.8333	Intermediate Similarity	NPC97322
0.8281	Intermediate Similarity	NPC182815
0.8281	Intermediate Similarity	NPC469677
0.8197	Intermediate Similarity	NPC32285
0.8182	Intermediate Similarity	NPC27438
0.8154	Intermediate Similarity	NPC477856
0.8154	Intermediate Similarity	NPC214770
0.8154	Intermediate Similarity	NPC282593
0.8154	Intermediate Similarity	NPC35734
0.8154	Intermediate Similarity	NPC159577
0.8103	Intermediate Similarity	NPC20603
0.8095	Intermediate Similarity	NPC323005
0.807	Intermediate Similarity	NPC63396
0.807	Intermediate Similarity	NPC202850
0.803	Intermediate Similarity	NPC181204
0.803	Intermediate Similarity	NPC115023
0.803	Intermediate Similarity	NPC470078
0.8	Intermediate Similarity	NPC143834
0.8	Intermediate Similarity	NPC285594
0.8	Intermediate Similarity	NPC139397
0.8	Intermediate Similarity	NPC96551
0.7969	Intermediate Similarity	NPC475523
0.7966	Intermediate Similarity	NPC115385
0.791	Intermediate Similarity	NPC251705
0.791	Intermediate Similarity	NPC474228
0.791	Intermediate Similarity	NPC470045
0.791	Intermediate Similarity	NPC303613
0.791	Intermediate Similarity	NPC470044
0.7903	Intermediate Similarity	NPC197238
0.7903	Intermediate Similarity	NPC202118
0.7895	Intermediate Similarity	NPC474141
0.7879	Intermediate Similarity	NPC2634
0.7879	Intermediate Similarity	NPC260040
0.7879	Intermediate Similarity	NPC307176
0.7879	Intermediate Similarity	NPC265782
0.7879	Intermediate Similarity	NPC40574
0.7879	Intermediate Similarity	NPC251929
0.7869	Intermediate Similarity	NPC127582
0.7857	Intermediate Similarity	NPC236623
0.7846	Intermediate Similarity	NPC469688
0.7794	Intermediate Similarity	NPC309852
0.7794	Intermediate Similarity	NPC329866
0.7794	Intermediate Similarity	NPC474796
0.7794	Intermediate Similarity	NPC474797
0.7778	Intermediate Similarity	NPC469662
0.7761	Intermediate Similarity	NPC54123
0.7761	Intermediate Similarity	NPC234707
0.7727	Intermediate Similarity	NPC162867
0.7727	Intermediate Similarity	NPC256846
0.7727	Intermediate Similarity	NPC61702
0.7681	Intermediate Similarity	NPC251435
0.7681	Intermediate Similarity	NPC293803
0.7679	Intermediate Similarity	NPC116906
0.7667	Intermediate Similarity	NPC193695
0.7656	Intermediate Similarity	NPC251118
0.7647	Intermediate Similarity	NPC92909
0.7647	Intermediate Similarity	NPC107783
0.7627	Intermediate Similarity	NPC200258
0.7627	Intermediate Similarity	NPC275472
0.7619	Intermediate Similarity	NPC472306
0.7619	Intermediate Similarity	NPC167256
0.7593	Intermediate Similarity	NPC49088
0.7586	Intermediate Similarity	NPC296311
0.7586	Intermediate Similarity	NPC268564
0.7576	Intermediate Similarity	NPC39157
0.7576	Intermediate Similarity	NPC82477
0.7576	Intermediate Similarity	NPC296697
0.7576	Intermediate Similarity	NPC142754
0.7571	Intermediate Similarity	NPC69408
0.7541	Intermediate Similarity	NPC27610
0.7541	Intermediate Similarity	NPC56905
0.7538	Intermediate Similarity	NPC43300
0.7538	Intermediate Similarity	NPC39462
0.7538	Intermediate Similarity	NPC168824
0.7538	Intermediate Similarity	NPC96812
0.7538	Intermediate Similarity	NPC189917
0.7538	Intermediate Similarity	NPC107704
0.7536	Intermediate Similarity	NPC469691
0.7536	Intermediate Similarity	NPC167049
0.7536	Intermediate Similarity	NPC255021
0.75	Intermediate Similarity	NPC5701
0.75	Intermediate Similarity	NPC6697
0.75	Intermediate Similarity	NPC305501
0.75	Intermediate Similarity	NPC285371
0.75	Intermediate Similarity	NPC475124
0.7465	Intermediate Similarity	NPC91665
0.7463	Intermediate Similarity	NPC286814
0.7458	Intermediate Similarity	NPC95581
0.7455	Intermediate Similarity	NPC323445
0.7429	Intermediate Similarity	NPC473171
0.7429	Intermediate Similarity	NPC255650
0.7424	Intermediate Similarity	NPC20181
0.7424	Intermediate Similarity	NPC220210
0.7419	Intermediate Similarity	NPC276764
0.7419	Intermediate Similarity	NPC472304
0.7377	Intermediate Similarity	NPC192427
0.7368	Intermediate Similarity	NPC32351
0.7361	Intermediate Similarity	NPC82635
0.7361	Intermediate Similarity	NPC470052
0.7361	Intermediate Similarity	NPC228911
0.7344	Intermediate Similarity	NPC288253
0.7324	Intermediate Similarity	NPC469793
0.7324	Intermediate Similarity	NPC469796
0.7324	Intermediate Similarity	NPC226242
0.7324	Intermediate Similarity	NPC469646
0.7321	Intermediate Similarity	NPC91962
0.7313	Intermediate Similarity	NPC469679
0.7313	Intermediate Similarity	NPC188292
0.7313	Intermediate Similarity	NPC155198
0.7313	Intermediate Similarity	NPC87141
0.7313	Intermediate Similarity	NPC310992
0.7313	Intermediate Similarity	NPC260474
0.7302	Intermediate Similarity	NPC270042
0.7288	Intermediate Similarity	NPC45283
0.726	Intermediate Similarity	NPC477371
0.726	Intermediate Similarity	NPC469690
0.726	Intermediate Similarity	NPC90965
0.726	Intermediate Similarity	NPC170793
0.726	Intermediate Similarity	NPC215843
0.7258	Intermediate Similarity	NPC170799
0.7258	Intermediate Similarity	NPC308108
0.7258	Intermediate Similarity	NPC311852
0.7246	Intermediate Similarity	NPC223187
0.7246	Intermediate Similarity	NPC190035
0.7241	Intermediate Similarity	NPC64866
0.7231	Intermediate Similarity	NPC4638
0.7222	Intermediate Similarity	NPC470557
0.7213	Intermediate Similarity	NPC473733
0.7206	Intermediate Similarity	NPC477857
0.7193	Intermediate Similarity	NPC145311
0.7183	Intermediate Similarity	NPC77501
0.7183	Intermediate Similarity	NPC475771
0.7183	Intermediate Similarity	NPC469669
0.7183	Intermediate Similarity	NPC469678
0.7164	Intermediate Similarity	NPC176107
0.7162	Intermediate Similarity	NPC474509
0.7143	Intermediate Similarity	NPC5698
0.7143	Intermediate Similarity	NPC470237
0.7143	Intermediate Similarity	NPC474488
0.7143	Intermediate Similarity	NPC8610
0.7143	Intermediate Similarity	NPC262558
0.7123	Intermediate Similarity	NPC469996
0.7121	Intermediate Similarity	NPC268039
0.7121	Intermediate Similarity	NPC470329
0.7119	Intermediate Similarity	NPC471751
0.7101	Intermediate Similarity	NPC151045
0.7101	Intermediate Similarity	NPC246722
0.7067	Intermediate Similarity	NPC4166
0.7067	Intermediate Similarity	NPC147066
0.7067	Intermediate Similarity	NPC201912
0.7067	Intermediate Similarity	NPC38350
0.7067	Intermediate Similarity	NPC477372
0.7042	Intermediate Similarity	NPC206875
0.7031	Intermediate Similarity	NPC252809
0.7031	Intermediate Similarity	NPC323153
0.7027	Intermediate Similarity	NPC469620
0.7015	Intermediate Similarity	NPC154728
0.7015	Intermediate Similarity	NPC92327
0.7015	Intermediate Similarity	NPC126899
0.7015	Intermediate Similarity	NPC304665
0.7015	Intermediate Similarity	NPC176171
0.7	Intermediate Similarity	NPC23117
0.7	Intermediate Similarity	NPC225467
0.7	Intermediate Similarity	NPC304983
0.7	Intermediate Similarity	NPC133253
0.6986	Remote Similarity	NPC276769
0.6984	Remote Similarity	NPC60772
0.6974	Remote Similarity	NPC311092
0.6974	Remote Similarity	NPC240302
0.6974	Remote Similarity	NPC260956
0.6974	Remote Similarity	NPC469805
0.6974	Remote Similarity	NPC142253
0.6974	Remote Similarity	NPC3511
0.6974	Remote Similarity	NPC256750
0.6974	Remote Similarity	NPC20262
0.6974	Remote Similarity	NPC133391
0.6974	Remote Similarity	NPC469804
0.6974	Remote Similarity	NPC472239
0.6974	Remote Similarity	NPC320514
0.6944	Remote Similarity	NPC65650
0.6944	Remote Similarity	NPC474011
0.6912	Remote Similarity	NPC193770
0.6912	Remote Similarity	NPC60120
0.6912	Remote Similarity	NPC278895
0.6901	Remote Similarity	NPC56747

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 NPC230823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	3224
0.2-0.3	4176
0.3-0.4	1032
0.4-0.5	306
0.5-0.6	164
0.6-0.7	57
0.7-0.8	10
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
0.8125	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4137	Phase 3
0.7879	Intermediate Similarity	NPD4691	Approved
0.7879	Intermediate Similarity	NPD4747	Approved
0.7794	Intermediate Similarity	NPD5733	Approved
0.7761	Intermediate Similarity	NPD5276	Approved
0.7536	Intermediate Similarity	NPD4687	Approved
0.7536	Intermediate Similarity	NPD4058	Approved
0.7258	Intermediate Similarity	NPD287	Approved
0.7123	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD344	Approved
0.6842	Remote Similarity	NPD345	Approved
0.6842	Remote Similarity	NPD343	Approved
0.6795	Remote Similarity	NPD4786	Approved
0.6792	Remote Similarity	NPD5783	Phase 3
0.6765	Remote Similarity	NPD7331	Phase 2
0.6753	Remote Similarity	NPD4223	Phase 3
0.6753	Remote Similarity	NPD4221	Approved
0.6753	Remote Similarity	NPD3667	Approved
0.6709	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7521	Approved
0.6625	Remote Similarity	NPD6098	Approved
0.6625	Remote Similarity	NPD7334	Approved
0.6625	Remote Similarity	NPD6409	Approved
0.6625	Remote Similarity	NPD7146	Approved
0.6625	Remote Similarity	NPD6684	Approved
0.6625	Remote Similarity	NPD5330	Approved
0.6582	Remote Similarity	NPD3133	Approved
0.6582	Remote Similarity	NPD3666	Approved
0.6582	Remote Similarity	NPD3665	Phase 1
0.6582	Remote Similarity	NPD4197	Approved
0.6582	Remote Similarity	NPD3668	Phase 3
0.6494	Remote Similarity	NPD5368	Approved
0.6463	Remote Similarity	NPD6903	Approved
0.6463	Remote Similarity	NPD6672	Approved
0.6463	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5737	Approved
0.6447	Remote Similarity	NPD3617	Approved
0.642	Remote Similarity	NPD4689	Approved
0.642	Remote Similarity	NPD4693	Phase 3
0.642	Remote Similarity	NPD4694	Approved
0.642	Remote Similarity	NPD5279	Phase 3
0.642	Remote Similarity	NPD4688	Approved
0.642	Remote Similarity	NPD3618	Phase 1
0.642	Remote Similarity	NPD5280	Approved
0.642	Remote Similarity	NPD5205	Approved
0.642	Remote Similarity	NPD4690	Approved
0.642	Remote Similarity	NPD5690	Phase 2
0.642	Remote Similarity	NPD4138	Approved
0.641	Remote Similarity	NPD5369	Approved
0.6386	Remote Similarity	NPD5328	Approved
0.6386	Remote Similarity	NPD6904	Approved
0.6386	Remote Similarity	NPD6673	Approved
0.6386	Remote Similarity	NPD6080	Approved
0.6377	Remote Similarity	NPD7341	Phase 2
0.6329	Remote Similarity	NPD4270	Approved
0.6329	Remote Similarity	NPD4269	Approved
0.6329	Remote Similarity	NPD6435	Approved
0.6282	Remote Similarity	NPD4695	Discontinued
0.6282	Remote Similarity	NPD4252	Approved
0.6265	Remote Similarity	NPD5208	Approved
0.6265	Remote Similarity	NPD4518	Approved
0.625	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD6922	Approved
0.625	Remote Similarity	NPD5362	Discontinued
0.6235	Remote Similarity	NPD6079	Approved
0.6235	Remote Similarity	NPD6050	Approved
0.622	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD8028	Phase 2
0.6203	Remote Similarity	NPD4139	Approved
0.6203	Remote Similarity	NPD4692	Approved
0.619	Remote Similarity	NPD4753	Phase 2
0.6164	Remote Similarity	NPD7143	Approved
0.6164	Remote Similarity	NPD7144	Approved
0.6163	Remote Similarity	NPD6399	Phase 3
0.6129	Remote Similarity	NPD29	Approved
0.6129	Remote Similarity	NPD28	Approved
0.6118	Remote Similarity	NPD5207	Approved
0.6118	Remote Similarity	NPD5692	Phase 3
0.6118	Remote Similarity	NPD4096	Approved
0.6118	Remote Similarity	NPD5785	Approved
0.6098	Remote Similarity	NPD5363	Approved
0.6081	Remote Similarity	NPD4243	Approved
0.6081	Remote Similarity	NPD7152	Approved
0.6081	Remote Similarity	NPD7151	Approved
0.6081	Remote Similarity	NPD7150	Approved
0.6053	Remote Similarity	NPD8039	Approved
0.6049	Remote Similarity	NPD4788	Approved
0.6047	Remote Similarity	NPD5694	Approved
0.6047	Remote Similarity	NPD5281	Approved
0.6047	Remote Similarity	NPD5284	Approved
0.6047	Remote Similarity	NPD5693	Phase 1
0.6024	Remote Similarity	NPD4519	Discontinued
0.6024	Remote Similarity	NPD4623	Approved
0.6024	Remote Similarity	NPD5786	Approved
0.6023	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4202	Approved
0.5949	Remote Similarity	NPD4195	Approved
0.5926	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD6924	Approved
0.5921	Remote Similarity	NPD4785	Approved
0.5921	Remote Similarity	NPD4784	Approved
0.5921	Remote Similarity	NPD6926	Approved
0.5909	Remote Similarity	NPD6001	Approved
0.5889	Remote Similarity	NPD6084	Phase 2
0.5889	Remote Similarity	NPD6083	Phase 2
0.5875	Remote Similarity	NPD4821	Approved
0.5875	Remote Similarity	NPD4820	Approved
0.5875	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD4822	Approved
0.5875	Remote Similarity	NPD4819	Approved
0.5854	Remote Similarity	NPD5332	Approved
0.5854	Remote Similarity	NPD5331	Approved
0.5854	Remote Similarity	NPD7154	Phase 3
0.5846	Remote Similarity	NPD3196	Approved
0.5846	Remote Similarity	NPD4266	Approved
0.5846	Remote Similarity	NPD3195	Phase 2
0.5846	Remote Similarity	NPD3194	Approved
0.5844	Remote Similarity	NPD7339	Approved
0.5844	Remote Similarity	NPD6942	Approved
0.5843	Remote Similarity	NPD5695	Phase 3
0.5843	Remote Similarity	NPD4629	Approved
0.5843	Remote Similarity	NPD5210	Approved
0.5833	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD4268	Approved
0.5823	Remote Similarity	NPD4271	Approved
0.5806	Remote Similarity	NPD8262	Approved
0.5802	Remote Similarity	NPD857	Phase 3
0.5802	Remote Similarity	NPD4790	Discontinued
0.5795	Remote Similarity	NPD5133	Approved
0.5778	Remote Similarity	NPD4697	Phase 3
0.5778	Remote Similarity	NPD5221	Approved
0.5778	Remote Similarity	NPD5222	Approved
0.5778	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6933	Approved
0.5765	Remote Similarity	NPD3573	Approved
0.5758	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD5209	Approved
0.573	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4191	Approved
0.5714	Remote Similarity	NPD4193	Approved
0.5714	Remote Similarity	NPD1694	Approved
0.5714	Remote Similarity	NPD4194	Approved
0.5714	Remote Similarity	NPD4192	Approved
0.5714	Remote Similarity	NPD5173	Approved
0.5714	Remote Similarity	NPD4755	Approved
0.5696	Remote Similarity	NPD6925	Approved
0.5696	Remote Similarity	NPD6932	Approved
0.5696	Remote Similarity	NPD5776	Phase 2
0.5692	Remote Similarity	NPD3172	Approved
0.5682	Remote Similarity	NPD7515	Phase 2
0.5679	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD4219	Approved
0.5667	Remote Similarity	NPD5654	Approved
0.5652	Remote Similarity	NPD5696	Approved
0.5641	Remote Similarity	NPD4190	Phase 3
0.5641	Remote Similarity	NPD5275	Approved
0.5634	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7145	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