NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.14
Volume:	281.368
LogP:	3.176
LogD:	3.219
LogS:	-4.464
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.844
Synthetic Accessibility Score:	3.497
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.699
MDCK Permeability:	1.6524296370334923e-05
Pgp-inhibitor:	0.148
Pgp-substrate:	0.52
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.458

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	70.955322265625%
Volume Distribution (VD):	1.967
Pgp-substrate:	22.670360565185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.647
CYP1A2-substrate:	0.568
CYP2C19-inhibitor:	0.469
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.358
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.483
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	6.918
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.627
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.4
Skin Sensitization:	0.86
Carcinogencity:	0.088
Eye Corrosion:	0.017
Eye Irritation:	0.118
Respiratory Toxicity:	0.741

Download Data

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

Natural Product: NPC312560

Natural Product ID:	NPC312560
*Common Name:**	Lacinilene C Methyl Ether
IUPAC Name:	(1R)-1-hydroxy-7-methoxy-1,6-dimethyl-4-propan-2-ylnaphthalen-2-one
Synonyms:	lacinilene C methyl ether
Standard InCHIKey:	VMEKKHYIQYOLHA-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C16H20O3/c1-9(2)11-7-15(17)16(4,18)13-8-14(19-5)10(3)6-12(11)13/h6-9,18H,1-5H3/t16-/m1/s1
SMILES:	COc1cc2c(cc1C)C(=CC(=O)[C@]2(C)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2206801
PubChem CID:	108125
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32770	sterculia tavia	Species	Malvaceae	Eukaryota	n.a.	Madagascar Rain Forest	n.a.	PMID[23149304]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30931559]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	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
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	4000.0	nM	PMID[488083]

☑ 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 NPC312560 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	337
0.1-0.2	1537
0.2-0.3	3372
0.3-0.4	8862
0.4-0.5	10011
0.5-0.6	4080
0.6-0.7	9186
0.7-0.8	5081
0.8-0.85	199
0.85-0.9	20
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC470725
0.9528	High Similarity	NPC253488
0.9242	High Similarity	NPC471670
0.9173	High Similarity	NPC470722
0.9173	High Similarity	NPC470721
0.9173	High Similarity	NPC156888
0.9173	High Similarity	NPC6100
0.9167	High Similarity	NPC22644
0.9127	High Similarity	NPC273683
0.8963	High Similarity	NPC475104
0.8915	High Similarity	NPC474737
0.8864	High Similarity	NPC239134
0.8841	High Similarity	NPC201297
0.8837	High Similarity	NPC123506
0.8797	High Similarity	NPC183103
0.8731	High Similarity	NPC59459
0.8722	High Similarity	NPC164295
0.8676	High Similarity	NPC475549
0.8623	High Similarity	NPC470407
0.8615	High Similarity	NPC199273
0.8615	High Similarity	NPC75432
0.8613	High Similarity	NPC186647
0.8613	High Similarity	NPC290601
0.8605	High Similarity	NPC282577
0.8593	High Similarity	NPC263817
0.8582	High Similarity	NPC471451
0.8582	High Similarity	NPC279596
0.8571	High Similarity	NPC171460
0.8571	High Similarity	NPC206028
0.8529	High Similarity	NPC27394
0.8529	High Similarity	NPC213122
0.8489	Intermediate Similarity	NPC477408
0.8444	Intermediate Similarity	NPC205360
0.844	Intermediate Similarity	NPC11314
0.8421	Intermediate Similarity	NPC477211
0.8421	Intermediate Similarity	NPC477212
0.8421	Intermediate Similarity	NPC72667
0.8421	Intermediate Similarity	NPC319422
0.8421	Intermediate Similarity	NPC477214
0.8385	Intermediate Similarity	NPC154696
0.8382	Intermediate Similarity	NPC165612
0.8382	Intermediate Similarity	NPC251549
0.837	Intermediate Similarity	NPC108129
0.8358	Intermediate Similarity	NPC96024
0.8346	Intermediate Similarity	NPC254492
0.8345	Intermediate Similarity	NPC98804
0.8345	Intermediate Similarity	NPC474556
0.8345	Intermediate Similarity	NPC301341
0.8345	Intermediate Similarity	NPC472841
0.8333	Intermediate Similarity	NPC474766
0.8333	Intermediate Similarity	NPC22222
0.8333	Intermediate Similarity	NPC281513
0.8333	Intermediate Similarity	NPC111088
0.8322	Intermediate Similarity	NPC309169
0.8322	Intermediate Similarity	NPC196941
0.8322	Intermediate Similarity	NPC471305
0.8321	Intermediate Similarity	NPC78307
0.8321	Intermediate Similarity	NPC49441
0.8309	Intermediate Similarity	NPC471851
0.8299	Intermediate Similarity	NPC472838
0.8299	Intermediate Similarity	NPC306011
0.8288	Intermediate Similarity	NPC329933
0.8288	Intermediate Similarity	NPC80370
0.8284	Intermediate Similarity	NPC69424
0.8284	Intermediate Similarity	NPC176130
0.8284	Intermediate Similarity	NPC78364
0.8284	Intermediate Similarity	NPC84672
0.8276	Intermediate Similarity	NPC478018
0.8276	Intermediate Similarity	NPC34802
0.8276	Intermediate Similarity	NPC58373
0.8271	Intermediate Similarity	NPC477213
0.8271	Intermediate Similarity	NPC470726
0.8264	Intermediate Similarity	NPC28632
0.8264	Intermediate Similarity	NPC478019
0.8264	Intermediate Similarity	NPC225351
0.8261	Intermediate Similarity	NPC202225
0.8252	Intermediate Similarity	NPC158871
0.8252	Intermediate Similarity	NPC53016
0.8252	Intermediate Similarity	NPC84266
0.824	Intermediate Similarity	NPC470723
0.8235	Intermediate Similarity	NPC245395
0.8235	Intermediate Similarity	NPC198305
0.8231	Intermediate Similarity	NPC475718
0.8231	Intermediate Similarity	NPC478121
0.8222	Intermediate Similarity	NPC3009
0.8214	Intermediate Similarity	NPC284184
0.8209	Intermediate Similarity	NPC15837
0.82	Intermediate Similarity	NPC474360
0.8194	Intermediate Similarity	NPC260152
0.8194	Intermediate Similarity	NPC471600
0.8194	Intermediate Similarity	NPC472836
0.8194	Intermediate Similarity	NPC477409
0.8188	Intermediate Similarity	NPC470406
0.8182	Intermediate Similarity	NPC164947
0.8182	Intermediate Similarity	NPC94076
0.8182	Intermediate Similarity	NPC182255
0.8176	Intermediate Similarity	NPC230848
0.8175	Intermediate Similarity	NPC474143
0.8175	Intermediate Similarity	NPC474246
0.8168	Intermediate Similarity	NPC129176
0.8168	Intermediate Similarity	NPC32322
0.8168	Intermediate Similarity	NPC259703
0.8162	Intermediate Similarity	NPC303910
0.8162	Intermediate Similarity	NPC276238
0.8151	Intermediate Similarity	NPC52692
0.8151	Intermediate Similarity	NPC478163
0.8134	Intermediate Similarity	NPC137750
0.8133	Intermediate Similarity	NPC471456
0.8129	Intermediate Similarity	NPC477210
0.8125	Intermediate Similarity	NPC316691
0.8125	Intermediate Similarity	NPC3732
0.8121	Intermediate Similarity	NPC470340
0.812	Intermediate Similarity	NPC471187
0.812	Intermediate Similarity	NPC135062
0.8116	Intermediate Similarity	NPC239302
0.8108	Intermediate Similarity	NPC158866
0.8108	Intermediate Similarity	NPC150928
0.8108	Intermediate Similarity	NPC58310
0.8108	Intermediate Similarity	NPC295977
0.8108	Intermediate Similarity	NPC225854
0.8105	Intermediate Similarity	NPC219686
0.8102	Intermediate Similarity	NPC196621
0.8102	Intermediate Similarity	NPC27659
0.8088	Intermediate Similarity	NPC201419
0.8088	Intermediate Similarity	NPC181675
0.8085	Intermediate Similarity	NPC119542
0.8085	Intermediate Similarity	NPC475957
0.8085	Intermediate Similarity	NPC24394
0.8082	Intermediate Similarity	NPC163846
0.8082	Intermediate Similarity	NPC225173
0.8074	Intermediate Similarity	NPC470724
0.8074	Intermediate Similarity	NPC177925
0.8067	Intermediate Similarity	NPC472799
0.8058	Intermediate Similarity	NPC470871
0.8058	Intermediate Similarity	NPC477139
0.8056	Intermediate Similarity	NPC232021
0.8056	Intermediate Similarity	NPC192597
0.8056	Intermediate Similarity	NPC176030
0.8056	Intermediate Similarity	NPC69755
0.8056	Intermediate Similarity	NPC169214
0.8056	Intermediate Similarity	NPC141817
0.8056	Intermediate Similarity	NPC229218
0.8056	Intermediate Similarity	NPC40118
0.8056	Intermediate Similarity	NPC126534
0.8054	Intermediate Similarity	NPC75377
0.8054	Intermediate Similarity	NPC474417
0.8054	Intermediate Similarity	NPC478148
0.8054	Intermediate Similarity	NPC144283
0.8054	Intermediate Similarity	NPC149526
0.8047	Intermediate Similarity	NPC114144
0.8045	Intermediate Similarity	NPC121168
0.8045	Intermediate Similarity	NPC152946
0.8043	Intermediate Similarity	NPC258073
0.8043	Intermediate Similarity	NPC477412
0.8042	Intermediate Similarity	NPC136649
0.8042	Intermediate Similarity	NPC168471
0.8042	Intermediate Similarity	NPC109232
0.8042	Intermediate Similarity	NPC165172
0.8041	Intermediate Similarity	NPC288036
0.8041	Intermediate Similarity	NPC97029
0.8041	Intermediate Similarity	NPC97028
0.8041	Intermediate Similarity	NPC65589
0.8041	Intermediate Similarity	NPC100985
0.8041	Intermediate Similarity	NPC158338
0.8039	Intermediate Similarity	NPC313368
0.8029	Intermediate Similarity	NPC59654
0.8027	Intermediate Similarity	NPC289042
0.8027	Intermediate Similarity	NPC56433
0.8027	Intermediate Similarity	NPC190648
0.8027	Intermediate Similarity	NPC126767
0.8027	Intermediate Similarity	NPC312929
0.8027	Intermediate Similarity	NPC125801
0.8027	Intermediate Similarity	NPC118027
0.8027	Intermediate Similarity	NPC245584
0.8026	Intermediate Similarity	NPC474637
0.8015	Intermediate Similarity	NPC121104
0.8015	Intermediate Similarity	NPC470841
0.8015	Intermediate Similarity	NPC428300
0.8014	Intermediate Similarity	NPC474630
0.8014	Intermediate Similarity	NPC194847
0.8014	Intermediate Similarity	NPC232996
0.8014	Intermediate Similarity	NPC328623
0.8014	Intermediate Similarity	NPC86524
0.8014	Intermediate Similarity	NPC21797
0.8013	Intermediate Similarity	NPC478159
0.8013	Intermediate Similarity	NPC478161
0.8	Intermediate Similarity	NPC470338
0.8	Intermediate Similarity	NPC76119
0.8	Intermediate Similarity	NPC470337
0.8	Intermediate Similarity	NPC232387
0.8	Intermediate Similarity	NPC51824
0.8	Intermediate Similarity	NPC224884
0.8	Intermediate Similarity	NPC180944
0.8	Intermediate Similarity	NPC87708
0.8	Intermediate Similarity	NPC274876
0.8	Intermediate Similarity	NPC4286
0.8	Intermediate Similarity	NPC209858
0.8	Intermediate Similarity	NPC209085
0.8	Intermediate Similarity	NPC297600
0.8	Intermediate Similarity	NPC163948

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 NPC312560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	988
0.2-0.3	1461
0.3-0.4	2511
0.4-0.5	2023
0.5-0.6	1124
0.6-0.7	608
0.7-0.8	111
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8372	Intermediate Similarity	NPD4626	Approved
0.8333	Intermediate Similarity	NPD1283	Approved
0.8295	Intermediate Similarity	NPD1651	Approved
0.8106	Intermediate Similarity	NPD1281	Approved
0.8015	Intermediate Similarity	NPD5691	Approved
0.7986	Intermediate Similarity	NPD7003	Approved
0.791	Intermediate Similarity	NPD3972	Approved
0.7857	Intermediate Similarity	NPD2979	Phase 3
0.7832	Intermediate Similarity	NPD2935	Discontinued
0.7832	Intermediate Similarity	NPD6099	Approved
0.7832	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD2346	Discontinued
0.777	Intermediate Similarity	NPD2534	Approved
0.777	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2532	Approved
0.777	Intermediate Similarity	NPD2533	Approved
0.773	Intermediate Similarity	NPD4060	Phase 1
0.7724	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2932	Approved
0.7682	Intermediate Similarity	NPD7458	Discontinued
0.7664	Intermediate Similarity	NPD1876	Approved
0.7639	Intermediate Similarity	NPD2799	Discontinued
0.7622	Intermediate Similarity	NPD1607	Approved
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3226	Approved
0.7562	Intermediate Similarity	NPD7473	Discontinued
0.7557	Intermediate Similarity	NPD1241	Discontinued
0.7556	Intermediate Similarity	NPD3019	Approved
0.7554	Intermediate Similarity	NPD2798	Approved
0.7551	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6959	Discontinued
0.7519	Intermediate Similarity	NPD7340	Approved
0.7518	Intermediate Similarity	NPD1608	Approved
0.7484	Intermediate Similarity	NPD7819	Suspended
0.7484	Intermediate Similarity	NPD6232	Discontinued
0.7483	Intermediate Similarity	NPD1240	Approved
0.7482	Intermediate Similarity	NPD2797	Approved
0.7481	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2531	Phase 2
0.7466	Intermediate Similarity	NPD4476	Approved
0.7466	Intermediate Similarity	NPD4477	Approved
0.7466	Intermediate Similarity	NPD2438	Suspended
0.7465	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6355	Discontinued
0.7429	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1398	Phase 1
0.7415	Intermediate Similarity	NPD2344	Approved
0.7413	Intermediate Similarity	NPD8032	Phase 2
0.741	Intermediate Similarity	NPD6696	Suspended
0.7397	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4628	Phase 3
0.7379	Intermediate Similarity	NPD4097	Suspended
0.7379	Intermediate Similarity	NPD6651	Approved
0.7372	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6273	Approved
0.7351	Intermediate Similarity	NPD7390	Discontinued
0.7338	Intermediate Similarity	NPD4749	Approved
0.7319	Intermediate Similarity	NPD1201	Approved
0.7315	Intermediate Similarity	NPD2800	Approved
0.7313	Intermediate Similarity	NPD6671	Approved
0.7305	Intermediate Similarity	NPD4624	Approved
0.7299	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1778	Approved
0.7299	Intermediate Similarity	NPD17	Approved
0.7297	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1471	Phase 3
0.729	Intermediate Similarity	NPD7028	Phase 2
0.7285	Intermediate Similarity	NPD3300	Phase 2
0.7279	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7267	Intermediate Similarity	NPD3750	Approved
0.7266	Intermediate Similarity	NPD2233	Approved
0.7266	Intermediate Similarity	NPD2232	Approved
0.7266	Intermediate Similarity	NPD2230	Approved
0.7259	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5844	Phase 1
0.7254	Intermediate Similarity	NPD9494	Approved
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD2309	Approved
0.7218	Intermediate Similarity	NPD7635	Approved
0.7215	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7644	Approved
0.7194	Intermediate Similarity	NPD1611	Approved
0.719	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6599	Discontinued
0.7179	Intermediate Similarity	NPD4380	Phase 2
0.7162	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD5710	Approved
0.716	Intermediate Similarity	NPD5711	Approved
0.7153	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD2424	Discontinued
0.7125	Intermediate Similarity	NPD7075	Discontinued
0.7124	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4140	Approved
0.7122	Intermediate Similarity	NPD3496	Discontinued
0.7122	Intermediate Similarity	NPD3026	Approved
0.7122	Intermediate Similarity	NPD3023	Approved
0.7114	Intermediate Similarity	NPD2796	Approved
0.7113	Intermediate Similarity	NPD3267	Approved
0.7113	Intermediate Similarity	NPD1470	Approved
0.7113	Intermediate Similarity	NPD3266	Approved
0.7103	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7985	Registered
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3025	Approved
0.7101	Intermediate Similarity	NPD3024	Approved
0.7089	Intermediate Similarity	NPD1934	Approved
0.7089	Intermediate Similarity	NPD37	Approved
0.708	Intermediate Similarity	NPD5536	Phase 2
0.7078	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5762	Approved
0.7067	Intermediate Similarity	NPD5763	Approved
0.7067	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6663	Approved
0.7052	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3748	Approved
0.7044	Intermediate Similarity	NPD2801	Approved
0.7037	Intermediate Similarity	NPD5283	Phase 1
0.7032	Intermediate Similarity	NPD5049	Phase 3
0.7029	Intermediate Similarity	NPD9545	Approved
0.7025	Intermediate Similarity	NPD7411	Suspended
0.702	Intermediate Similarity	NPD1549	Phase 2
0.7014	Intermediate Similarity	NPD5736	Approved
0.7014	Intermediate Similarity	NPD2861	Phase 2
0.7013	Intermediate Similarity	NPD1511	Approved
0.7013	Intermediate Similarity	NPD6799	Approved
0.7007	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3620	Phase 2
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD3847	Discontinued
0.7	Intermediate Similarity	NPD5406	Approved
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD2354	Approved
0.6992	Remote Similarity	NPD4750	Phase 3
0.6988	Remote Similarity	NPD7177	Discontinued
0.6987	Remote Similarity	NPD7427	Discontinued
0.6986	Remote Similarity	NPD3764	Approved
0.6986	Remote Similarity	NPD411	Approved
0.6981	Remote Similarity	NPD6801	Discontinued
0.6978	Remote Similarity	NPD5585	Approved
0.6974	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5327	Phase 3
0.6972	Remote Similarity	NPD1669	Approved
0.697	Remote Similarity	NPD6166	Phase 2
0.697	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4966	Approved
0.6957	Remote Similarity	NPD4965	Approved
0.6957	Remote Similarity	NPD4967	Phase 2
0.6954	Remote Similarity	NPD6002	Phase 3
0.6954	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6005	Phase 3
0.6954	Remote Similarity	NPD6004	Phase 3
0.6951	Remote Similarity	NPD7229	Phase 3
0.695	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7236	Approved
0.6943	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6233	Phase 2
0.6936	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5494	Approved
0.6933	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD288	Approved
0.6929	Remote Similarity	NPD2667	Approved
0.6929	Remote Similarity	NPD2668	Approved
0.6928	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4110	Phase 3
0.6919	Remote Similarity	NPD8150	Discontinued
0.6913	Remote Similarity	NPD6353	Approved
0.6913	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2157	Approved
0.6908	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1894	Discontinued
0.6901	Remote Similarity	NPD9717	Approved
0.6901	Remote Similarity	NPD1481	Phase 2
0.6894	Remote Similarity	NPD3134	Approved
0.6894	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3142	Approved
0.6892	Remote Similarity	NPD3140	Approved
0.6892	Remote Similarity	NPD2238	Phase 2
0.6892	Remote Similarity	NPD4307	Phase 2
0.6889	Remote Similarity	NPD228	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