NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	257.918
LogP:	2.355
LogD:	1.96
LogS:	-2.288
# Rotatable Bonds:	2
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	4.342
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.513
MDCK Permeability:	5.943041469436139e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.351
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	59.58669662475586%
Volume Distribution (VD):	0.98
Pgp-substrate:	49.079498291015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.163
CYP1A2-substrate:	0.264
CYP2C19-inhibitor:	0.234
CYP2C19-substrate:	0.636
CYP2C9-inhibitor:	0.089
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	14.645
Half-life (T1/2):	0.613

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.722
Maximum Recommended Daily Dose:	0.081
Skin Sensitization:	0.925
Carcinogencity:	0.861
Eye Corrosion:	0.98
Eye Irritation:	0.972
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC212210

Natural Product ID:	NPC212210
*Common Name:**	Chiloscypha-2,7-Dione
IUPAC Name:	(1S,7S,7aS)-7,7a-dimethyl-1-(2-methylprop-2-enoyl)-2,3,6,7-tetrahydro-1H-inden-5-one
Synonyms:	Chiloscypha-2,7-Dione
Standard InCHIKey:	UQEVJIYDECNMHF-PSOPSSQASA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-9(2)14(17)13-6-5-11-8-12(16)7-10(3)15(11,13)4/h8,10,13H,1,5-7H2,2-4H3/t10-,13+,15+/m0/s1
SMILES:	O=C1C[C@H](C)[C@@]2(C(=C1)CC[C@@H]2C(=O)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462804
PubChem CID:	10513764
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO8475	Chiloscyphus rivularis	Species	Lophocoleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9463110]
NPO8475	Chiloscyphus rivularis	Species	Lophocoleaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	500.0	ug ml-1	PMID[499347]

☑ 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 NPC212210 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	148
0.1-0.2	2400
0.2-0.3	14487
0.3-0.4	12998
0.4-0.5	7419
0.5-0.6	3877
0.6-0.7	1132
0.7-0.8	184
0.8-0.85	30
0.85-0.9	13
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9516	High Similarity	NPC475523
0.9333	High Similarity	NPC213152
0.918	High Similarity	NPC32285
0.918	High Similarity	NPC165695
0.9077	High Similarity	NPC2634
0.9077	High Similarity	NPC265782
0.9077	High Similarity	NPC251929
0.9	High Similarity	NPC259261
0.8939	High Similarity	NPC54123
0.8923	High Similarity	NPC139397
0.8871	High Similarity	NPC288253
0.8852	High Similarity	NPC127582
0.8852	High Similarity	NPC25853
0.8833	High Similarity	NPC94991
0.8833	High Similarity	NPC311852
0.8833	High Similarity	NPC266295
0.8806	High Similarity	NPC474228
0.8806	High Similarity	NPC303613
0.8788	High Similarity	NPC260040
0.8788	High Similarity	NPC307176
0.8676	High Similarity	NPC309852
0.8657	High Similarity	NPC5701
0.8636	High Similarity	NPC256846
0.8594	High Similarity	NPC251118
0.8529	High Similarity	NPC470045
0.8529	High Similarity	NPC251705
0.8529	High Similarity	NPC470044
0.8525	High Similarity	NPC30215
0.8507	High Similarity	NPC159577
0.8507	High Similarity	NPC282593
0.8507	High Similarity	NPC35734
0.8485	Intermediate Similarity	NPC260474
0.8485	Intermediate Similarity	NPC188292
0.8485	Intermediate Similarity	NPC155198
0.8485	Intermediate Similarity	NPC87141
0.8438	Intermediate Similarity	NPC6697
0.8438	Intermediate Similarity	NPC475124
0.8438	Intermediate Similarity	NPC473902
0.8438	Intermediate Similarity	NPC285371
0.8429	Intermediate Similarity	NPC69408
0.8413	Intermediate Similarity	NPC475795
0.8413	Intermediate Similarity	NPC97322
0.8406	Intermediate Similarity	NPC474797
0.8406	Intermediate Similarity	NPC329866
0.8406	Intermediate Similarity	NPC255021
0.8406	Intermediate Similarity	NPC474796
0.8387	Intermediate Similarity	NPC276764
0.8387	Intermediate Similarity	NPC472304
0.8382	Intermediate Similarity	NPC305501
0.8382	Intermediate Similarity	NPC115023
0.8382	Intermediate Similarity	NPC234707
0.8382	Intermediate Similarity	NPC181204
0.8382	Intermediate Similarity	NPC304983
0.8361	Intermediate Similarity	NPC230823
0.8361	Intermediate Similarity	NPC55004
0.8361	Intermediate Similarity	NPC267626
0.8361	Intermediate Similarity	NPC49575
0.8308	Intermediate Similarity	NPC470329
0.8305	Intermediate Similarity	NPC23117
0.8286	Intermediate Similarity	NPC293803
0.8281	Intermediate Similarity	NPC472306
0.8226	Intermediate Similarity	NPC308108
0.8226	Intermediate Similarity	NPC170799
0.8226	Intermediate Similarity	NPC27610
0.8226	Intermediate Similarity	NPC56905
0.8209	Intermediate Similarity	NPC20610
0.8209	Intermediate Similarity	NPC310992
0.8182	Intermediate Similarity	NPC323005
0.8169	Intermediate Similarity	NPC469793
0.8169	Intermediate Similarity	NPC469796
0.8125	Intermediate Similarity	NPC60565
0.8116	Intermediate Similarity	NPC474562
0.8095	Intermediate Similarity	NPC96551
0.8095	Intermediate Similarity	NPC285594
0.8088	Intermediate Similarity	NPC61702
0.8088	Intermediate Similarity	NPC162867
0.8088	Intermediate Similarity	NPC182815
0.8082	Intermediate Similarity	NPC170793
0.8082	Intermediate Similarity	NPC90965
0.8065	Intermediate Similarity	NPC192427
0.8065	Intermediate Similarity	NPC115385
0.806	Intermediate Similarity	NPC4370
0.806	Intermediate Similarity	NPC290350
0.8028	Intermediate Similarity	NPC473171
0.8028	Intermediate Similarity	NPC255650
0.8	Intermediate Similarity	NPC268564
0.8	Intermediate Similarity	NPC197238
0.8	Intermediate Similarity	NPC14002
0.8	Intermediate Similarity	NPC202118
0.8	Intermediate Similarity	NPC167256
0.8	Intermediate Similarity	NPC296311
0.8	Intermediate Similarity	NPC474141
0.7973	Intermediate Similarity	NPC45495
0.7973	Intermediate Similarity	NPC474509
0.7971	Intermediate Similarity	NPC246722
0.7971	Intermediate Similarity	NPC151045
0.7969	Intermediate Similarity	NPC270042
0.7966	Intermediate Similarity	NPC64866
0.7945	Intermediate Similarity	NPC228911
0.791	Intermediate Similarity	NPC176171
0.791	Intermediate Similarity	NPC92327
0.7903	Intermediate Similarity	NPC20603
0.7879	Intermediate Similarity	NPC469662
0.7869	Intermediate Similarity	NPC5626
0.7857	Intermediate Similarity	NPC190035
0.7857	Intermediate Similarity	NPC21944
0.7857	Intermediate Similarity	NPC470078
0.7857	Intermediate Similarity	NPC223187
0.7838	Intermediate Similarity	NPC7232
0.7812	Intermediate Similarity	NPC143834
0.7797	Intermediate Similarity	NPC228776
0.7797	Intermediate Similarity	NPC116906
0.7797	Intermediate Similarity	NPC32351
0.7794	Intermediate Similarity	NPC176107
0.7778	Intermediate Similarity	NPC476346
0.7778	Intermediate Similarity	NPC193695
0.7763	Intermediate Similarity	NPC142253
0.7763	Intermediate Similarity	NPC3511
0.7763	Intermediate Similarity	NPC472239
0.7746	Intermediate Similarity	NPC56747
0.7746	Intermediate Similarity	NPC109576
0.7746	Intermediate Similarity	NPC130016
0.7746	Intermediate Similarity	NPC180015
0.7742	Intermediate Similarity	NPC275472
0.7742	Intermediate Similarity	NPC200258
0.7714	Intermediate Similarity	NPC477856
0.7714	Intermediate Similarity	NPC214770
0.7714	Intermediate Similarity	NPC40574
0.7703	Intermediate Similarity	NPC469996
0.7681	Intermediate Similarity	NPC469688
0.7671	Intermediate Similarity	NPC470525
0.7671	Intermediate Similarity	NPC1254
0.7667	Intermediate Similarity	NPC236623
0.7656	Intermediate Similarity	NPC60772
0.7639	Intermediate Similarity	NPC20025
0.7632	Intermediate Similarity	NPC477372
0.7632	Intermediate Similarity	NPC136150
0.7619	Intermediate Similarity	NPC473733
0.7612	Intermediate Similarity	NPC150162
0.7612	Intermediate Similarity	NPC4638
0.7606	Intermediate Similarity	NPC133253
0.7606	Intermediate Similarity	NPC225467
0.7581	Intermediate Similarity	NPC63396
0.7581	Intermediate Similarity	NPC202850
0.7571	Intermediate Similarity	NPC286814
0.7571	Intermediate Similarity	NPC477857
0.7568	Intermediate Similarity	NPC97377
0.7564	Intermediate Similarity	NPC87552
0.7541	Intermediate Similarity	NPC471751
0.7534	Intermediate Similarity	NPC114236
0.7534	Intermediate Similarity	NPC65650
0.7534	Intermediate Similarity	NPC251435
0.7532	Intermediate Similarity	NPC193347
0.7532	Intermediate Similarity	NPC320514
0.7532	Intermediate Similarity	NPC469805
0.7532	Intermediate Similarity	NPC469804
0.7532	Intermediate Similarity	NPC469799
0.7532	Intermediate Similarity	NPC472867
0.7532	Intermediate Similarity	NPC469806
0.75	Intermediate Similarity	NPC176819
0.75	Intermediate Similarity	NPC469797
0.75	Intermediate Similarity	NPC58970
0.75	Intermediate Similarity	NPC472478
0.75	Intermediate Similarity	NPC469798
0.75	Intermediate Similarity	NPC163984
0.7468	Intermediate Similarity	NPC29447
0.7468	Intermediate Similarity	NPC8571
0.7467	Intermediate Similarity	NPC189485
0.7467	Intermediate Similarity	NPC62336
0.7467	Intermediate Similarity	NPC82635
0.7467	Intermediate Similarity	NPC115515
0.7467	Intermediate Similarity	NPC470052
0.7467	Intermediate Similarity	NPC74410
0.7467	Intermediate Similarity	NPC475994
0.7436	Intermediate Similarity	NPC41539
0.7436	Intermediate Similarity	NPC3856
0.7436	Intermediate Similarity	NPC474976
0.7436	Intermediate Similarity	NPC474790
0.7436	Intermediate Similarity	NPC279639
0.7432	Intermediate Similarity	NPC474463
0.7432	Intermediate Similarity	NPC473223
0.7432	Intermediate Similarity	NPC180886
0.7432	Intermediate Similarity	NPC263582
0.7429	Intermediate Similarity	NPC296697
0.7429	Intermediate Similarity	NPC82477
0.7429	Intermediate Similarity	NPC39157
0.7429	Intermediate Similarity	NPC142754
0.7419	Intermediate Similarity	NPC69898
0.7419	Intermediate Similarity	NPC37644
0.7419	Intermediate Similarity	NPC45283
0.7419	Intermediate Similarity	NPC295777
0.7397	Intermediate Similarity	NPC219232
0.7397	Intermediate Similarity	NPC167049
0.7397	Intermediate Similarity	NPC211641
0.7397	Intermediate Similarity	NPC128346
0.7397	Intermediate Similarity	NPC469691
0.7377	Intermediate Similarity	NPC27438
0.7368	Intermediate Similarity	NPC476177
0.7368	Intermediate Similarity	NPC472490
0.7368	Intermediate Similarity	NPC27817

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 NPC212210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	2758
0.2-0.3	4380
0.3-0.4	1258
0.4-0.5	302
0.5-0.6	207
0.6-0.7	80
0.7-0.8	8
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9077	High Similarity	NPD4691	Approved
0.8923	High Similarity	NPD4137	Phase 3
0.8788	High Similarity	NPD4747	Approved
0.8676	High Similarity	NPD4058	Approved
0.8657	High Similarity	NPD5276	Approved
0.8406	Intermediate Similarity	NPD4687	Approved
0.8406	Intermediate Similarity	NPD5733	Approved
0.8226	Intermediate Similarity	NPD287	Approved
0.8209	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4223	Phase 3
0.7532	Intermediate Similarity	NPD4221	Approved
0.7375	Intermediate Similarity	NPD5690	Phase 2
0.7342	Intermediate Similarity	NPD4197	Approved
0.7342	Intermediate Similarity	NPD3666	Approved
0.7342	Intermediate Similarity	NPD3133	Approved
0.7342	Intermediate Similarity	NPD3665	Phase 1
0.7273	Intermediate Similarity	NPD4695	Discontinued
0.725	Intermediate Similarity	NPD5329	Approved
0.7237	Intermediate Similarity	NPD3617	Approved
0.716	Intermediate Similarity	NPD4688	Approved
0.716	Intermediate Similarity	NPD6409	Approved
0.716	Intermediate Similarity	NPD7146	Approved
0.716	Intermediate Similarity	NPD6684	Approved
0.716	Intermediate Similarity	NPD4689	Approved
0.716	Intermediate Similarity	NPD4694	Approved
0.716	Intermediate Similarity	NPD3618	Phase 1
0.716	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5279	Phase 3
0.716	Intermediate Similarity	NPD5205	Approved
0.716	Intermediate Similarity	NPD5280	Approved
0.716	Intermediate Similarity	NPD7334	Approved
0.716	Intermediate Similarity	NPD5330	Approved
0.716	Intermediate Similarity	NPD4138	Approved
0.716	Intermediate Similarity	NPD4690	Approved
0.716	Intermediate Similarity	NPD4693	Phase 3
0.716	Intermediate Similarity	NPD7521	Approved
0.7089	Intermediate Similarity	NPD3667	Approved
0.6988	Remote Similarity	NPD5208	Approved
0.6988	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6903	Approved
0.6988	Remote Similarity	NPD5737	Approved
0.6988	Remote Similarity	NPD6672	Approved
0.6962	Remote Similarity	NPD8028	Phase 2
0.6941	Remote Similarity	NPD6079	Approved
0.6923	Remote Similarity	NPD4195	Approved
0.6914	Remote Similarity	NPD3668	Phase 3
0.6914	Remote Similarity	NPD4786	Approved
0.6905	Remote Similarity	NPD5328	Approved
0.6905	Remote Similarity	NPD4753	Phase 2
0.6905	Remote Similarity	NPD6904	Approved
0.6905	Remote Similarity	NPD6080	Approved
0.6905	Remote Similarity	NPD6673	Approved
0.6901	Remote Similarity	NPD7331	Phase 2
0.6824	Remote Similarity	NPD4096	Approved
0.6824	Remote Similarity	NPD5692	Phase 3
0.6824	Remote Similarity	NPD5207	Approved
0.6786	Remote Similarity	NPD4518	Approved
0.6747	Remote Similarity	NPD4519	Discontinued
0.6747	Remote Similarity	NPD4623	Approved
0.6747	Remote Similarity	NPD6098	Approved
0.6744	Remote Similarity	NPD5281	Approved
0.6744	Remote Similarity	NPD6050	Approved
0.6744	Remote Similarity	NPD5284	Approved
0.6744	Remote Similarity	NPD5694	Approved
0.6744	Remote Similarity	NPD5693	Phase 1
0.6705	Remote Similarity	NPD5210	Approved
0.6705	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3573	Approved
0.6629	Remote Similarity	NPD5222	Approved
0.6629	Remote Similarity	NPD5221	Approved
0.6629	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6001	Approved
0.6556	Remote Similarity	NPD5173	Approved
0.6543	Remote Similarity	NPD4692	Approved
0.6543	Remote Similarity	NPD4139	Approved
0.6528	Remote Similarity	NPD7341	Phase 2
0.6517	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5695	Phase 3
0.6477	Remote Similarity	NPD5133	Approved
0.6444	Remote Similarity	NPD4697	Phase 3
0.6429	Remote Similarity	NPD1694	Approved
0.6413	Remote Similarity	NPD5285	Approved
0.6413	Remote Similarity	NPD4696	Approved
0.6413	Remote Similarity	NPD5286	Approved
0.6386	Remote Similarity	NPD4788	Approved
0.6375	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4755	Approved
0.6374	Remote Similarity	NPD6084	Phase 2
0.6374	Remote Similarity	NPD6083	Phase 2
0.6344	Remote Similarity	NPD5223	Approved
0.6338	Remote Similarity	NPD4192	Approved
0.6338	Remote Similarity	NPD4191	Approved
0.6338	Remote Similarity	NPD4194	Approved
0.6338	Remote Similarity	NPD4193	Approved
0.6333	Remote Similarity	NPD5654	Approved
0.6304	Remote Similarity	NPD5696	Approved
0.6292	Remote Similarity	NPD6399	Phase 3
0.6277	Remote Similarity	NPD5225	Approved
0.6277	Remote Similarity	NPD4633	Approved
0.6277	Remote Similarity	NPD5211	Phase 2
0.6277	Remote Similarity	NPD5091	Approved
0.6277	Remote Similarity	NPD5224	Approved
0.6277	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4700	Approved
0.6235	Remote Similarity	NPD1696	Phase 3
0.622	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5175	Approved
0.6211	Remote Similarity	NPD5174	Approved
0.6196	Remote Similarity	NPD5959	Approved
0.619	Remote Similarity	NPD344	Approved
0.619	Remote Similarity	NPD343	Approved
0.619	Remote Similarity	NPD345	Approved
0.618	Remote Similarity	NPD7515	Phase 2
0.6176	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5141	Approved
0.6136	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5785	Approved
0.6064	Remote Similarity	NPD6404	Discontinued
0.6047	Remote Similarity	NPD5363	Approved
0.6044	Remote Similarity	NPD7900	Approved
0.6044	Remote Similarity	NPD7748	Approved
0.6044	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6052	Approved
0.6042	Remote Similarity	NPD4754	Approved
0.6026	Remote Similarity	NPD4243	Approved
0.6022	Remote Similarity	NPD3495	Discontinued
0.602	Remote Similarity	NPD5697	Approved
0.602	Remote Similarity	NPD6614	Approved
0.6	Remote Similarity	NPD8039	Approved
0.596	Remote Similarity	NPD4729	Approved
0.596	Remote Similarity	NPD5128	Approved
0.596	Remote Similarity	NPD5168	Approved
0.596	Remote Similarity	NPD6899	Approved
0.596	Remote Similarity	NPD6881	Approved
0.596	Remote Similarity	NPD6011	Approved
0.596	Remote Similarity	NPD4730	Approved
0.5934	Remote Similarity	NPD7631	Approved
0.5926	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4767	Approved
0.5918	Remote Similarity	NPD5739	Approved
0.5918	Remote Similarity	NPD6402	Approved
0.5918	Remote Similarity	NPD6675	Approved
0.5918	Remote Similarity	NPD4768	Approved
0.5918	Remote Similarity	NPD6008	Approved
0.5918	Remote Similarity	NPD7128	Approved
0.5914	Remote Similarity	NPD7614	Phase 1
0.5914	Remote Similarity	NPD7732	Phase 3
0.59	Remote Similarity	NPD6012	Approved
0.59	Remote Similarity	NPD6014	Approved
0.59	Remote Similarity	NPD6013	Approved
0.5882	Remote Similarity	NPD5209	Approved
0.5875	Remote Similarity	NPD4784	Approved
0.5875	Remote Similarity	NPD4785	Approved
0.5859	Remote Similarity	NPD5701	Approved
0.5859	Remote Similarity	NPD6412	Phase 2
0.5851	Remote Similarity	NPD7902	Approved
0.5842	Remote Similarity	NPD5248	Approved
0.5842	Remote Similarity	NPD5169	Approved
0.5842	Remote Similarity	NPD6883	Approved
0.5842	Remote Similarity	NPD7102	Approved
0.5842	Remote Similarity	NPD5251	Approved
0.5842	Remote Similarity	NPD7290	Approved
0.5842	Remote Similarity	NPD5250	Approved
0.5842	Remote Similarity	NPD5249	Phase 3
0.5842	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5247	Approved
0.5842	Remote Similarity	NPD4634	Approved
0.5842	Remote Similarity	NPD5135	Approved
0.5833	Remote Similarity	NPD5368	Approved
0.5824	Remote Similarity	NPD7609	Phase 3
0.5806	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6942	Approved
0.5802	Remote Similarity	NPD5275	Approved
0.5802	Remote Similarity	NPD4190	Phase 3
0.5802	Remote Similarity	NPD7339	Approved
0.58	Remote Similarity	NPD7320	Approved
0.5784	Remote Similarity	NPD6649	Approved
0.5784	Remote Similarity	NPD5127	Approved
0.5784	Remote Similarity	NPD5217	Approved
0.5784	Remote Similarity	NPD5216	Approved
0.5784	Remote Similarity	NPD6847	Approved
0.5784	Remote Similarity	NPD6650	Approved
0.5784	Remote Similarity	NPD5215	Approved
0.5784	Remote Similarity	NPD8130	Phase 1
0.5784	Remote Similarity	NPD6617	Approved
0.5784	Remote Similarity	NPD6869	Approved
0.5769	Remote Similarity	NPD6923	Approved
0.5769	Remote Similarity	NPD6922	Approved
0.5765	Remote Similarity	NPD5369	Approved
0.5761	Remote Similarity	NPD1508	Approved
0.5743	Remote Similarity	NPD6373	Approved
0.5743	Remote Similarity	NPD6372	Approved
0.5733	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.573	Remote Similarity	NPD650	Approved
0.5728	Remote Similarity	NPD8297	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