NPASS Compound

Structure

NPC97322 OpenBabel07101718192D 22 23 0 0 1 0 0 0 0 0999 V2000 0.1974 -1.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3915 -1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6263 -2.0690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1062 2.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9733 0.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4855 0.3844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1138 -0.5440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2962 1.3663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3004 -1.1716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4344 -0.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 1.9987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1538 1.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3980 -0.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2992 -1.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6062 2.0900 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 2.6343 2.3258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5082 0.8612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0712 1.2127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5868 3.3247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5037 0.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 15 17 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	341.761
LogP:	3.676
LogD:	3.142
LogS:	-4.741
# Rotatable Bonds:	1
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	4.792
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.63
MDCK Permeability:	2.9445371183101088e-05
Pgp-inhibitor:	0.11
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.348
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.712
Plasma Protein Binding (PPB):	80.66878509521484%
Volume Distribution (VD):	0.912
Pgp-substrate:	13.547524452209473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.586
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.573
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	11.852
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.244
Carcinogencity:	0.883
Eye Corrosion:	0.027
Eye Irritation:	0.015
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC97322

Natural Product ID:	NPC97322
*Common Name:**	(1R*)-Dolabella-4(16),7,11(12)-Triene-3,13-Dione
IUPAC Name:	(3aR,9E)-3a,10-dimethyl-6-methylidene-1-propan-2-yl-3,4,7,8,11,12-hexahydrocyclopenta[11]annulene-2,5-dione
Synonyms:
Standard InCHIKey:	MVHNKCBUOUIONY-CDXDBMBRSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-13(2)19-16-10-9-14(3)7-6-8-15(4)17(21)11-20(16,5)12-18(19)22/h7,13H,4,6,8-12H2,1-3,5H3/b14-7+/t20-/m1/s1
SMILES:	CC(C)C1=C2CC/C(=C/CCC(=C)C(=O)C[C@]2(C)CC1=O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459256
PubChem CID:	44567222
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
NPO27081	Clavularia inflata	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[11520220]
NPO27081	Clavularia inflata	Species	Clavulariidae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[460841]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[460841]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.89	ug ml-1	PMID[460841]

☑ 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 NPC97322 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	234
0.1-0.2	3079
0.2-0.3	15858
0.3-0.4	13039
0.4-0.5	6761
0.5-0.6	2956
0.6-0.7	634
0.7-0.8	108
0.8-0.85	20
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9016	High Similarity	NPC473902
0.9	High Similarity	NPC475795
0.8983	High Similarity	NPC259261
0.8852	High Similarity	NPC32285
0.8833	High Similarity	NPC25853
0.8814	High Similarity	NPC94991
0.8814	High Similarity	NPC266295
0.8596	High Similarity	NPC296311
0.8596	High Similarity	NPC474141
0.8594	High Similarity	NPC475523
0.8548	High Similarity	NPC167256
0.85	High Similarity	NPC30215
0.8413	Intermediate Similarity	NPC212210
0.8333	Intermediate Similarity	NPC193695
0.8333	Intermediate Similarity	NPC49575
0.8333	Intermediate Similarity	NPC61702
0.8333	Intermediate Similarity	NPC55004
0.8333	Intermediate Similarity	NPC267626
0.8333	Intermediate Similarity	NPC162867
0.8333	Intermediate Similarity	NPC230823
0.8254	Intermediate Similarity	NPC165695
0.8167	Intermediate Similarity	NPC20603
0.8103	Intermediate Similarity	NPC471751
0.8065	Intermediate Similarity	NPC285594
0.8065	Intermediate Similarity	NPC96551
0.806	Intermediate Similarity	NPC256846
0.8	Intermediate Similarity	NPC470329
0.8	Intermediate Similarity	NPC216791
0.8	Intermediate Similarity	NPC251118
0.8	Intermediate Similarity	NPC275472
0.7966	Intermediate Similarity	NPC45283
0.7941	Intermediate Similarity	NPC151045
0.7941	Intermediate Similarity	NPC265782
0.7941	Intermediate Similarity	NPC251929
0.7941	Intermediate Similarity	NPC246722
0.7941	Intermediate Similarity	NPC2634
0.7895	Intermediate Similarity	NPC145311
0.7826	Intermediate Similarity	NPC54123
0.7812	Intermediate Similarity	NPC213152
0.7794	Intermediate Similarity	NPC139397
0.7742	Intermediate Similarity	NPC115385
0.7714	Intermediate Similarity	NPC303613
0.7714	Intermediate Similarity	NPC474228
0.7692	Intermediate Similarity	NPC288253
0.7681	Intermediate Similarity	NPC307176
0.7681	Intermediate Similarity	NPC260040
0.7656	Intermediate Similarity	NPC127582
0.7647	Intermediate Similarity	NPC469688
0.7647	Intermediate Similarity	NPC188292
0.7647	Intermediate Similarity	NPC155198
0.7647	Intermediate Similarity	NPC469679
0.7647	Intermediate Similarity	NPC260474
0.7647	Intermediate Similarity	NPC87141
0.7619	Intermediate Similarity	NPC311852
0.7619	Intermediate Similarity	NPC56905
0.7619	Intermediate Similarity	NPC27610
0.7606	Intermediate Similarity	NPC309852
0.7606	Intermediate Similarity	NPC474797
0.7606	Intermediate Similarity	NPC474796
0.7606	Intermediate Similarity	NPC329866
0.7571	Intermediate Similarity	NPC5701
0.7571	Intermediate Similarity	NPC181204
0.7571	Intermediate Similarity	NPC474562
0.7568	Intermediate Similarity	NPC90965
0.7544	Intermediate Similarity	NPC262558
0.7544	Intermediate Similarity	NPC8610
0.7541	Intermediate Similarity	NPC63396
0.7541	Intermediate Similarity	NPC202850
0.7538	Intermediate Similarity	NPC260573
0.7538	Intermediate Similarity	NPC60565
0.75	Intermediate Similarity	NPC474011
0.75	Intermediate Similarity	NPC469678
0.75	Intermediate Similarity	NPC469669
0.75	Intermediate Similarity	NPC475771
0.75	Intermediate Similarity	NPC251435
0.75	Intermediate Similarity	NPC473171
0.75	Intermediate Similarity	NPC143834
0.7465	Intermediate Similarity	NPC470044
0.7465	Intermediate Similarity	NPC251705
0.7465	Intermediate Similarity	NPC470045
0.746	Intermediate Similarity	NPC192427
0.7458	Intermediate Similarity	NPC32351
0.7458	Intermediate Similarity	NPC228776
0.7429	Intermediate Similarity	NPC159577
0.7429	Intermediate Similarity	NPC35734
0.7429	Intermediate Similarity	NPC282593
0.7424	Intermediate Similarity	NPC472306
0.7397	Intermediate Similarity	NPC469796
0.7397	Intermediate Similarity	NPC469793
0.7397	Intermediate Similarity	NPC69408
0.7391	Intermediate Similarity	NPC310992
0.7391	Intermediate Similarity	NPC476614
0.7377	Intermediate Similarity	NPC268564
0.7361	Intermediate Similarity	NPC469691
0.7361	Intermediate Similarity	NPC255021
0.7361	Intermediate Similarity	NPC167049
0.7333	Intermediate Similarity	NPC27438
0.7333	Intermediate Similarity	NPC64866
0.7324	Intermediate Similarity	NPC115023
0.7324	Intermediate Similarity	NPC234707
0.7324	Intermediate Similarity	NPC305501
0.7324	Intermediate Similarity	NPC223187
0.7313	Intermediate Similarity	NPC150162
0.7313	Intermediate Similarity	NPC4638
0.7313	Intermediate Similarity	NPC475124
0.7313	Intermediate Similarity	NPC285371
0.7313	Intermediate Similarity	NPC6697
0.7308	Intermediate Similarity	NPC238197
0.7302	Intermediate Similarity	NPC473733
0.7286	Intermediate Similarity	NPC469677
0.726	Intermediate Similarity	NPC255650
0.726	Intermediate Similarity	NPC293803
0.7241	Intermediate Similarity	NPC100380
0.7241	Intermediate Similarity	NPC471752
0.7237	Intermediate Similarity	NPC164218
0.7231	Intermediate Similarity	NPC276764
0.7231	Intermediate Similarity	NPC472304
0.7206	Intermediate Similarity	NPC474304
0.7206	Intermediate Similarity	NPC474329
0.72	Intermediate Similarity	NPC474056
0.72	Intermediate Similarity	NPC115515
0.72	Intermediate Similarity	NPC228911
0.7179	Intermediate Similarity	NPC65350
0.7167	Intermediate Similarity	NPC118788
0.7167	Intermediate Similarity	NPC176819
0.7167	Intermediate Similarity	NPC163984
0.7167	Intermediate Similarity	NPC58970
0.7167	Intermediate Similarity	NPC116906
0.7164	Intermediate Similarity	NPC202118
0.7164	Intermediate Similarity	NPC197238
0.7162	Intermediate Similarity	NPC469646
0.7143	Intermediate Similarity	NPC20610
0.7143	Intermediate Similarity	NPC188789
0.7123	Intermediate Similarity	NPC20025
0.7105	Intermediate Similarity	NPC170793
0.7101	Intermediate Similarity	NPC323005
0.7097	Intermediate Similarity	NPC23117
0.7097	Intermediate Similarity	NPC37644
0.7083	Intermediate Similarity	NPC304983
0.7083	Intermediate Similarity	NPC29328
0.7083	Intermediate Similarity	NPC133253
0.7083	Intermediate Similarity	NPC190035
0.7083	Intermediate Similarity	NPC21944
0.7077	Intermediate Similarity	NPC60772
0.7077	Intermediate Similarity	NPC308108
0.7077	Intermediate Similarity	NPC170799
0.7059	Intermediate Similarity	NPC469662
0.7051	Intermediate Similarity	NPC472867
0.7049	Intermediate Similarity	NPC236623
0.7042	Intermediate Similarity	NPC182815
0.7042	Intermediate Similarity	NPC469914
0.7042	Intermediate Similarity	NPC67608
0.7027	Intermediate Similarity	NPC77501
0.7027	Intermediate Similarity	NPC476346
0.7013	Intermediate Similarity	NPC474509
0.7	Intermediate Similarity	NPC4370
0.7	Intermediate Similarity	NPC290350
0.7	Intermediate Similarity	NPC142649
0.7	Intermediate Similarity	NPC8571
0.6986	Remote Similarity	NPC474488
0.6986	Remote Similarity	NPC107783
0.6986	Remote Similarity	NPC92909
0.6986	Remote Similarity	NPC130016
0.6986	Remote Similarity	NPC109576
0.6986	Remote Similarity	NPC56747
0.6986	Remote Similarity	NPC180015
0.6984	Remote Similarity	NPC95581
0.6962	Remote Similarity	NPC41539
0.6962	Remote Similarity	NPC470165
0.6957	Remote Similarity	NPC183422
0.6949	Remote Similarity	NPC4079
0.6949	Remote Similarity	NPC14917
0.6949	Remote Similarity	NPC236355
0.6944	Remote Similarity	NPC214770
0.6944	Remote Similarity	NPC40574
0.6944	Remote Similarity	NPC477856
0.6933	Remote Similarity	NPC27205
0.6933	Remote Similarity	NPC40353
0.6933	Remote Similarity	NPC1254
0.6933	Remote Similarity	NPC110725
0.6933	Remote Similarity	NPC215481
0.6912	Remote Similarity	NPC322457
0.6885	Remote Similarity	NPC474391
0.6883	Remote Similarity	NPC469690
0.6875	Remote Similarity	NPC475796
0.6875	Remote Similarity	NPC149869
0.6875	Remote Similarity	NPC475100
0.6875	Remote Similarity	NPC200258
0.6875	Remote Similarity	NPC230527
0.6875	Remote Similarity	NPC7927
0.6866	Remote Similarity	NPC270042
0.6857	Remote Similarity	NPC197089
0.6857	Remote Similarity	NPC176171
0.6857	Remote Similarity	NPC154728
0.6857	Remote Similarity	NPC92327
0.6857	Remote Similarity	NPC304665
0.6857	Remote Similarity	NPC126899
0.6849	Remote Similarity	NPC470078
0.6849	Remote Similarity	NPC225467
0.6842	Remote Similarity	NPC276769

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 NPC97322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	3222
0.2-0.3	4129
0.3-0.4	1086
0.4-0.5	324
0.5-0.6	146
0.6-0.7	21
0.7-0.8	2
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
0.7941	Intermediate Similarity	NPD4691	Approved
0.7794	Intermediate Similarity	NPD4137	Phase 3
0.7681	Intermediate Similarity	NPD4747	Approved
0.7606	Intermediate Similarity	NPD4058	Approved
0.7571	Intermediate Similarity	NPD5276	Approved
0.7361	Intermediate Similarity	NPD4687	Approved
0.7361	Intermediate Similarity	NPD5733	Approved
0.7143	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD287	Approved
0.6857	Remote Similarity	NPD7331	Phase 2
0.675	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4223	Phase 3
0.6625	Remote Similarity	NPD4221	Approved
0.6582	Remote Similarity	NPD4695	Discontinued
0.6506	Remote Similarity	NPD5690	Phase 2
0.6479	Remote Similarity	NPD7341	Phase 2
0.6463	Remote Similarity	NPD3133	Approved
0.6463	Remote Similarity	NPD4197	Approved
0.6463	Remote Similarity	NPD3665	Phase 1
0.6463	Remote Similarity	NPD3666	Approved
0.6386	Remote Similarity	NPD5329	Approved
0.6329	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3617	Approved
0.631	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5279	Phase 3
0.631	Remote Similarity	NPD3618	Phase 1
0.631	Remote Similarity	NPD6409	Approved
0.631	Remote Similarity	NPD5205	Approved
0.631	Remote Similarity	NPD6684	Approved
0.631	Remote Similarity	NPD5330	Approved
0.631	Remote Similarity	NPD4519	Discontinued
0.631	Remote Similarity	NPD4689	Approved
0.631	Remote Similarity	NPD7521	Approved
0.631	Remote Similarity	NPD4688	Approved
0.631	Remote Similarity	NPD5280	Approved
0.631	Remote Similarity	NPD4623	Approved
0.631	Remote Similarity	NPD4690	Approved
0.631	Remote Similarity	NPD4693	Phase 3
0.631	Remote Similarity	NPD7146	Approved
0.631	Remote Similarity	NPD4138	Approved
0.631	Remote Similarity	NPD7334	Approved
0.631	Remote Similarity	NPD4694	Approved
0.6296	Remote Similarity	NPD8028	Phase 2
0.6292	Remote Similarity	NPD5210	Approved
0.6292	Remote Similarity	NPD4629	Approved
0.622	Remote Similarity	NPD5209	Approved
0.622	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3667	Approved
0.6197	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6672	Approved
0.6163	Remote Similarity	NPD5737	Approved
0.6163	Remote Similarity	NPD4518	Approved
0.6163	Remote Similarity	NPD6903	Approved
0.6163	Remote Similarity	NPD5208	Approved
0.6163	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6079	Approved
0.6119	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD5328	Approved
0.6092	Remote Similarity	NPD6904	Approved
0.6092	Remote Similarity	NPD6673	Approved
0.6092	Remote Similarity	NPD6080	Approved
0.6092	Remote Similarity	NPD4753	Phase 2
0.6071	Remote Similarity	NPD3668	Phase 3
0.6071	Remote Similarity	NPD4786	Approved
0.6056	Remote Similarity	NPD4194	Approved
0.6056	Remote Similarity	NPD4193	Approved
0.6056	Remote Similarity	NPD4192	Approved
0.6056	Remote Similarity	NPD4191	Approved
0.6049	Remote Similarity	NPD4195	Approved
0.6047	Remote Similarity	NPD3573	Approved
0.6034	Remote Similarity	NPD5783	Phase 3
0.6023	Remote Similarity	NPD4096	Approved
0.6023	Remote Similarity	NPD5785	Approved
0.6023	Remote Similarity	NPD5207	Approved
0.6023	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD1694	Approved
0.6	Remote Similarity	NPD5363	Approved
0.5976	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6050	Approved
0.5955	Remote Similarity	NPD5693	Phase 1
0.5955	Remote Similarity	NPD5694	Approved
0.5955	Remote Similarity	NPD5281	Approved
0.5955	Remote Similarity	NPD5284	Approved
0.593	Remote Similarity	NPD6098	Approved
0.5914	Remote Similarity	NPD5696	Approved
0.5895	Remote Similarity	NPD5091	Approved
0.5889	Remote Similarity	NPD4202	Approved
0.5873	Remote Similarity	NPD345	Approved
0.5873	Remote Similarity	NPD343	Approved
0.5873	Remote Similarity	NPD344	Approved
0.587	Remote Similarity	NPD5221	Approved
0.587	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5222	Approved
0.5824	Remote Similarity	NPD5282	Discontinued
0.5824	Remote Similarity	NPD6001	Approved
0.5806	Remote Similarity	NPD5173	Approved
0.5783	Remote Similarity	NPD5368	Approved
0.5765	Remote Similarity	NPD7154	Phase 3
0.5765	Remote Similarity	NPD5362	Discontinued
0.5765	Remote Similarity	NPD4788	Approved
0.5761	Remote Similarity	NPD5695	Phase 3
0.5761	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD29	Approved
0.5758	Remote Similarity	NPD28	Approved
0.575	Remote Similarity	NPD8039	Approved
0.5735	Remote Similarity	NPD9298	Approved
0.5714	Remote Similarity	NPD4139	Approved
0.5714	Remote Similarity	NPD5133	Approved
0.5714	Remote Similarity	NPD857	Phase 3
0.5714	Remote Similarity	NPD4692	Approved
0.5714	Remote Similarity	NPD5369	Approved
0.5699	Remote Similarity	NPD7614	Phase 1
0.5699	Remote Similarity	NPD4697	Phase 3
0.5699	Remote Similarity	NPD7732	Phase 3
0.5684	Remote Similarity	NPD5285	Approved
0.5684	Remote Similarity	NPD4696	Approved
0.5684	Remote Similarity	NPD5286	Approved
0.5657	Remote Similarity	NPD6614	Approved
0.5647	Remote Similarity	NPD4269	Approved
0.5647	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD6435	Approved
0.5647	Remote Similarity	NPD4270	Approved
0.5638	Remote Similarity	NPD6083	Phase 2
0.5638	Remote Similarity	NPD4755	Approved
0.5638	Remote Similarity	NPD6084	Phase 2
0.5632	Remote Similarity	NPD1696	Phase 3
0.5625	Remote Similarity	NPD5223	Approved
0.5604	Remote Similarity	NPD7515	Phase 2
0.56	Remote Similarity	NPD2685	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