NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	1.227
LogD:	1.101
LogS:	-3.518
# Rotatable Bonds:	2
TPSA:	52.99
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	5.38
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.658
MDCK Permeability:	2.5196266506100073e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	35.112274169921875%
Volume Distribution (VD):	1.346
Pgp-substrate:	70.81983184814453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.3
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.42
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	3.651
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.906
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.975
Carcinogencity:	0.358
Eye Corrosion:	0.449
Eye Irritation:	0.563
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: NPC281316

Natural Product ID:	NPC281316
*Common Name:**	Phomadecalin A
IUPAC Name:	(1aS,2R,7S,7aR,7bR)-1a-(3-hydroxyprop-1-en-2-yl)-7,7a-dimethyl-2,6,7,7b-tetrahydronaphtho[1,2-b]oxiren-2-ol
Synonyms:
Standard InCHIKey:	QINRUZADLMGSLB-BGJHODNPSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9-5-4-6-11-7-12(17)15(10(2)8-16)13(18-15)14(9,11)3/h4,6-7,9,12-13,16-17H,2,5,8H2,1,3H3/t9-,12+,13+,14+,15-/m0/s1
SMILES:	OCC(=C)[C@]12O[C@@H]2[C@]2(C(=C[C@H]1O)C=CC[C@@H]2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513546
PubChem CID:	10083350
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
NPO33418	Phoma sp. NRRL 25697	Species	Didymellaceae	Eukaryota	Hypoxylon stromata	n.a.	n.a.	PMID[11908990]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.0	mm	PMID[475929]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	18.0	mm	PMID[475929]

☑ 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 NPC281316 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	212
0.1-0.2	1420
0.2-0.3	4793
0.3-0.4	14023
0.4-0.5	13231
0.5-0.6	7085
0.6-0.7	1766
0.7-0.8	153
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC49783
0.9048	High Similarity	NPC255143
0.8989	High Similarity	NPC57664
0.8571	High Similarity	NPC471408
0.8421	Intermediate Similarity	NPC473624
0.8132	Intermediate Similarity	NPC471453
0.8111	Intermediate Similarity	NPC20946
0.8085	Intermediate Similarity	NPC261807
0.8022	Intermediate Similarity	NPC191323
0.8	Intermediate Similarity	NPC233295
0.7955	Intermediate Similarity	NPC83702
0.7931	Intermediate Similarity	NPC259858
0.7907	Intermediate Similarity	NPC474592
0.7895	Intermediate Similarity	NPC205143
0.7889	Intermediate Similarity	NPC245004
0.7889	Intermediate Similarity	NPC131329
0.7872	Intermediate Similarity	NPC8774
0.7849	Intermediate Similarity	NPC310013
0.7789	Intermediate Similarity	NPC12103
0.7789	Intermediate Similarity	NPC98457
0.7789	Intermediate Similarity	NPC288970
0.7789	Intermediate Similarity	NPC210717
0.7789	Intermediate Similarity	NPC103165
0.7789	Intermediate Similarity	NPC227583
0.7778	Intermediate Similarity	NPC473893
0.7766	Intermediate Similarity	NPC127718
0.7766	Intermediate Similarity	NPC65402
0.7753	Intermediate Similarity	NPC238485
0.7738	Intermediate Similarity	NPC171148
0.7738	Intermediate Similarity	NPC313179
0.7738	Intermediate Similarity	NPC69383
0.7727	Intermediate Similarity	NPC155521
0.7717	Intermediate Similarity	NPC128066
0.7717	Intermediate Similarity	NPC115607
0.7711	Intermediate Similarity	NPC265485
0.7711	Intermediate Similarity	NPC130665
0.7711	Intermediate Similarity	NPC220939
0.7692	Intermediate Similarity	NPC476948
0.7674	Intermediate Similarity	NPC68119
0.7674	Intermediate Similarity	NPC167891
0.7674	Intermediate Similarity	NPC13823
0.7674	Intermediate Similarity	NPC476314
0.7674	Intermediate Similarity	NPC83351
0.7674	Intermediate Similarity	NPC477089
0.766	Intermediate Similarity	NPC137461
0.766	Intermediate Similarity	NPC119379
0.7654	Intermediate Similarity	NPC96484
0.7647	Intermediate Similarity	NPC265588
0.7647	Intermediate Similarity	NPC170148
0.764	Intermediate Similarity	NPC470384
0.7634	Intermediate Similarity	NPC197107
0.7625	Intermediate Similarity	NPC267027
0.7619	Intermediate Similarity	NPC190859
0.7619	Intermediate Similarity	NPC471525
0.7619	Intermediate Similarity	NPC24590
0.7614	Intermediate Similarity	NPC474894
0.7604	Intermediate Similarity	NPC72204
0.759	Intermediate Similarity	NPC23954
0.7582	Intermediate Similarity	NPC125399
0.7561	Intermediate Similarity	NPC471560
0.7561	Intermediate Similarity	NPC329989
0.7561	Intermediate Similarity	NPC239373
0.7556	Intermediate Similarity	NPC474047
0.7556	Intermediate Similarity	NPC46320
0.7556	Intermediate Similarity	NPC231310
0.7527	Intermediate Similarity	NPC97103
0.75	Intermediate Similarity	NPC149224
0.7474	Intermediate Similarity	NPC307776
0.7473	Intermediate Similarity	NPC35933
0.7473	Intermediate Similarity	NPC274448
0.7471	Intermediate Similarity	NPC475980
0.747	Intermediate Similarity	NPC129630
0.747	Intermediate Similarity	NPC92801
0.7447	Intermediate Similarity	NPC291484
0.7447	Intermediate Similarity	NPC329596
0.7447	Intermediate Similarity	NPC11216
0.7447	Intermediate Similarity	NPC204188
0.7447	Intermediate Similarity	NPC3345
0.7447	Intermediate Similarity	NPC80561
0.7444	Intermediate Similarity	NPC49208
0.7444	Intermediate Similarity	NPC23748
0.7444	Intermediate Similarity	NPC475789
0.7439	Intermediate Similarity	NPC471238
0.7416	Intermediate Similarity	NPC471270
0.7416	Intermediate Similarity	NPC476646
0.7407	Intermediate Similarity	NPC326310
0.74	Intermediate Similarity	NPC11956
0.7396	Intermediate Similarity	NPC469491
0.7386	Intermediate Similarity	NPC471537
0.7381	Intermediate Similarity	NPC242992
0.7381	Intermediate Similarity	NPC471271
0.7381	Intermediate Similarity	NPC471272
0.7381	Intermediate Similarity	NPC471268
0.7381	Intermediate Similarity	NPC164022
0.7374	Intermediate Similarity	NPC38855
0.7374	Intermediate Similarity	NPC473510
0.7368	Intermediate Similarity	NPC97404
0.7368	Intermediate Similarity	NPC114389
0.7368	Intermediate Similarity	NPC41554
0.7363	Intermediate Similarity	NPC470077
0.7356	Intermediate Similarity	NPC91594
0.7356	Intermediate Similarity	NPC476703
0.7347	Intermediate Similarity	NPC473244
0.7347	Intermediate Similarity	NPC210337
0.734	Intermediate Similarity	NPC246028
0.734	Intermediate Similarity	NPC299527
0.734	Intermediate Similarity	NPC470361
0.734	Intermediate Similarity	NPC309310
0.7333	Intermediate Similarity	NPC477390
0.7333	Intermediate Similarity	NPC477385
0.7333	Intermediate Similarity	NPC87489
0.7333	Intermediate Similarity	NPC202389
0.7327	Intermediate Similarity	NPC23584
0.7317	Intermediate Similarity	NPC82337
0.7303	Intermediate Similarity	NPC96362
0.7303	Intermediate Similarity	NPC471266
0.7303	Intermediate Similarity	NPC95124
0.7303	Intermediate Similarity	NPC236707
0.73	Intermediate Similarity	NPC207885
0.73	Intermediate Similarity	NPC476896
0.7294	Intermediate Similarity	NPC68443
0.7292	Intermediate Similarity	NPC474792
0.7292	Intermediate Similarity	NPC67398
0.7292	Intermediate Similarity	NPC53555
0.7292	Intermediate Similarity	NPC91654
0.7284	Intermediate Similarity	NPC287339
0.7283	Intermediate Similarity	NPC266511
0.7283	Intermediate Similarity	NPC298595
0.7283	Intermediate Similarity	NPC157257
0.7283	Intermediate Similarity	NPC119001
0.7283	Intermediate Similarity	NPC290731
0.7283	Intermediate Similarity	NPC474189
0.7283	Intermediate Similarity	NPC477578
0.7283	Intermediate Similarity	NPC474349
0.7282	Intermediate Similarity	NPC469957
0.7282	Intermediate Similarity	NPC469959
0.7282	Intermediate Similarity	NPC472263
0.7282	Intermediate Similarity	NPC108682
0.7273	Intermediate Similarity	NPC312325
0.7273	Intermediate Similarity	NPC137587
0.7263	Intermediate Similarity	NPC295668
0.7263	Intermediate Similarity	NPC182136
0.7263	Intermediate Similarity	NPC220216
0.7263	Intermediate Similarity	NPC476226
0.7263	Intermediate Similarity	NPC92885
0.7263	Intermediate Similarity	NPC77796
0.7262	Intermediate Similarity	NPC34834
0.7253	Intermediate Similarity	NPC185605
0.7253	Intermediate Similarity	NPC237795
0.7253	Intermediate Similarity	NPC317458
0.7253	Intermediate Similarity	NPC477978
0.7253	Intermediate Similarity	NPC474634
0.7253	Intermediate Similarity	NPC82538
0.725	Intermediate Similarity	NPC83200
0.7245	Intermediate Similarity	NPC88009
0.7245	Intermediate Similarity	NPC284194
0.7245	Intermediate Similarity	NPC471765
0.7245	Intermediate Similarity	NPC473153
0.7245	Intermediate Similarity	NPC211810
0.7245	Intermediate Similarity	NPC221801
0.7241	Intermediate Similarity	NPC274079
0.7241	Intermediate Similarity	NPC106432
0.7241	Intermediate Similarity	NPC253190
0.7241	Intermediate Similarity	NPC477925
0.7234	Intermediate Similarity	NPC471952
0.7234	Intermediate Similarity	NPC280556
0.7234	Intermediate Similarity	NPC474668
0.7234	Intermediate Similarity	NPC133588
0.7234	Intermediate Similarity	NPC67872
0.7229	Intermediate Similarity	NPC276616
0.7228	Intermediate Similarity	NPC470571
0.7222	Intermediate Similarity	NPC474759
0.7222	Intermediate Similarity	NPC6707
0.7222	Intermediate Similarity	NPC474731
0.7222	Intermediate Similarity	NPC249423
0.7222	Intermediate Similarity	NPC474752
0.7222	Intermediate Similarity	NPC474683
0.7222	Intermediate Similarity	NPC470298
0.7222	Intermediate Similarity	NPC264245
0.7222	Intermediate Similarity	NPC7505
0.7222	Intermediate Similarity	NPC82986
0.7216	Intermediate Similarity	NPC472360
0.7216	Intermediate Similarity	NPC144202
0.7216	Intermediate Similarity	NPC472416
0.7209	Intermediate Similarity	NPC471797
0.7209	Intermediate Similarity	NPC201048
0.7209	Intermediate Similarity	NPC476366
0.7204	Intermediate Similarity	NPC61527
0.7204	Intermediate Similarity	NPC476217
0.72	Intermediate Similarity	NPC230546
0.72	Intermediate Similarity	NPC79303
0.7195	Intermediate Similarity	NPC202017
0.7191	Intermediate Similarity	NPC17550
0.7191	Intermediate Similarity	NPC31258
0.7191	Intermediate Similarity	NPC242767
0.7191	Intermediate Similarity	NPC476701
0.7188	Intermediate Similarity	NPC475441
0.7188	Intermediate Similarity	NPC124374
0.7188	Intermediate Similarity	NPC302584
0.7184	Intermediate Similarity	NPC29389

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 NPC281316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1740
0.2-0.3	3827
0.3-0.4	2309
0.4-0.5	861
0.5-0.6	165
0.6-0.7	46
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
0.7738	Intermediate Similarity	NPD8264	Approved
0.7312	Intermediate Similarity	NPD7524	Approved
0.7174	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5344	Discontinued
0.7065	Intermediate Similarity	NPD6695	Phase 3
0.7045	Intermediate Similarity	NPD6933	Approved
0.703	Intermediate Similarity	NPD6648	Approved
0.6961	Remote Similarity	NPD4159	Approved
0.6931	Remote Similarity	NPD4225	Approved
0.6923	Remote Similarity	NPD7332	Phase 2
0.6923	Remote Similarity	NPD6930	Phase 2
0.6923	Remote Similarity	NPD7514	Phase 3
0.6923	Remote Similarity	NPD6931	Approved
0.6914	Remote Similarity	NPD368	Approved
0.6907	Remote Similarity	NPD7838	Discovery
0.6889	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6902	Approved
0.6847	Remote Similarity	NPD7115	Discovery
0.6818	Remote Similarity	NPD6924	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6813	Remote Similarity	NPD7645	Phase 2
0.6813	Remote Similarity	NPD6929	Approved
0.6771	Remote Similarity	NPD7750	Discontinued
0.6768	Remote Similarity	NPD5779	Approved
0.6768	Remote Similarity	NPD5778	Approved
0.6739	Remote Similarity	NPD7509	Discontinued
0.6703	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6411	Approved
0.6598	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6925	Approved
0.6593	Remote Similarity	NPD6932	Approved
0.6593	Remote Similarity	NPD5776	Phase 2
0.6591	Remote Similarity	NPD7152	Approved
0.6591	Remote Similarity	NPD7150	Approved
0.6591	Remote Similarity	NPD7151	Approved
0.6562	Remote Similarity	NPD1696	Phase 3
0.6562	Remote Similarity	NPD6893	Approved
0.6559	Remote Similarity	NPD7525	Registered
0.6556	Remote Similarity	NPD6942	Approved
0.6556	Remote Similarity	NPD7339	Approved
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7087	Discontinued
0.6489	Remote Similarity	NPD6898	Phase 1
0.6477	Remote Similarity	NPD7144	Approved
0.6477	Remote Similarity	NPD7143	Approved
0.6465	Remote Similarity	NPD6101	Approved
0.6465	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6698	Approved
0.64	Remote Similarity	NPD46	Approved
0.6389	Remote Similarity	NPD6640	Phase 3
0.6383	Remote Similarity	NPD4748	Discontinued
0.6375	Remote Similarity	NPD342	Phase 1
0.6364	Remote Similarity	NPD6922	Approved
0.6364	Remote Similarity	NPD6923	Approved
0.6337	Remote Similarity	NPD7637	Suspended
0.6333	Remote Similarity	NPD4732	Discontinued
0.6325	Remote Similarity	NPD7503	Approved
0.6296	Remote Similarity	NPD4219	Approved
0.6289	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6683	Phase 2
0.625	Remote Similarity	NPD3667	Approved
0.6238	Remote Similarity	NPD3168	Discontinued
0.6226	Remote Similarity	NPD7639	Approved
0.6226	Remote Similarity	NPD7640	Approved
0.6211	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD8517	Approved
0.6186	Remote Similarity	NPD8515	Approved
0.6186	Remote Similarity	NPD8513	Phase 3
0.6186	Remote Similarity	NPD8516	Approved
0.6176	Remote Similarity	NPD7983	Approved
0.6161	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7638	Approved
0.6122	Remote Similarity	NPD4786	Approved
0.6111	Remote Similarity	NPD5211	Phase 2
0.6087	Remote Similarity	NPD4785	Approved
0.6087	Remote Similarity	NPD4784	Approved
0.6068	Remote Similarity	NPD7328	Approved
0.6068	Remote Similarity	NPD7327	Approved
0.6061	Remote Similarity	NPD1694	Approved
0.605	Remote Similarity	NPD8033	Approved
0.6022	Remote Similarity	NPD8039	Approved
0.6018	Remote Similarity	NPD6371	Approved
0.6017	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD3618	Phase 1
0.5982	Remote Similarity	NPD6686	Approved
0.598	Remote Similarity	NPD6051	Approved
0.5977	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD371	Approved
0.5966	Remote Similarity	NPD8294	Approved
0.5966	Remote Similarity	NPD8377	Approved
0.5962	Remote Similarity	NPD4202	Approved
0.5962	Remote Similarity	NPD6399	Phase 3
0.5935	Remote Similarity	NPD8074	Phase 3
0.5926	Remote Similarity	NPD5285	Approved
0.5926	Remote Similarity	NPD4696	Approved
0.5926	Remote Similarity	NPD5286	Approved
0.5922	Remote Similarity	NPD7136	Phase 2
0.5917	Remote Similarity	NPD8380	Approved
0.5917	Remote Similarity	NPD8379	Approved
0.5917	Remote Similarity	NPD8335	Approved
0.5917	Remote Similarity	NPD8378	Approved
0.5917	Remote Similarity	NPD8296	Approved
0.5913	Remote Similarity	NPD8297	Approved
0.5909	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5697	Approved
0.5888	Remote Similarity	NPD4755	Approved
0.5876	Remote Similarity	NPD4821	Approved
0.5876	Remote Similarity	NPD4820	Approved
0.5876	Remote Similarity	NPD4819	Approved
0.5876	Remote Similarity	NPD4822	Approved
0.5876	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4243	Approved
0.5865	Remote Similarity	NPD6079	Approved
0.5849	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4623	Approved
0.5842	Remote Similarity	NPD4519	Discontinued
0.5841	Remote Similarity	NPD6899	Approved
0.5841	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6881	Approved
0.5826	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5328	Approved
0.5818	Remote Similarity	NPD5224	Approved
0.5818	Remote Similarity	NPD5225	Approved
0.5818	Remote Similarity	NPD5226	Approved
0.5818	Remote Similarity	NPD4633	Approved
0.5804	Remote Similarity	NPD6675	Approved
0.5804	Remote Similarity	NPD7128	Approved
0.5804	Remote Similarity	NPD5739	Approved
0.5804	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD3666	Approved
0.58	Remote Similarity	NPD3665	Phase 1
0.58	Remote Similarity	NPD3133	Approved
0.5794	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6014	Approved
0.5789	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD6012	Approved
0.578	Remote Similarity	NPD4700	Approved
0.5773	Remote Similarity	NPD4195	Approved
0.5766	Remote Similarity	NPD5175	Approved
0.5766	Remote Similarity	NPD5174	Approved
0.5755	Remote Similarity	NPD7748	Approved
0.5752	Remote Similarity	NPD5701	Approved
0.5752	Remote Similarity	NPD6412	Phase 2
0.5741	Remote Similarity	NPD7902	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD4634	Approved
0.5739	Remote Similarity	NPD7102	Approved
0.5728	Remote Similarity	NPD4518	Approved
0.5727	Remote Similarity	NPD5223	Approved
0.5726	Remote Similarity	NPD4632	Approved
0.5726	Remote Similarity	NPD7507	Approved
0.5714	Remote Similarity	NPD5281	Approved
0.5714	Remote Similarity	NPD4198	Discontinued
0.5714	Remote Similarity	NPD5284	Approved
0.5714	Remote Similarity	NPD7515	Phase 2
0.5702	Remote Similarity	NPD6319	Approved
0.5702	Remote Similarity	NPD7320	Approved
0.5702	Remote Similarity	NPD6011	Approved
0.5702	Remote Similarity	NPD7741	Discontinued
0.5701	Remote Similarity	NPD5695	Phase 3
0.57	Remote Similarity	NPD7154	Phase 3
0.569	Remote Similarity	NPD8130	Phase 1
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6617	Approved
0.569	Remote Similarity	NPD6649	Approved
0.5686	Remote Similarity	NPD4694	Approved
0.5686	Remote Similarity	NPD5280	Approved
0.5684	Remote Similarity	NPD4190	Phase 3
0.5684	Remote Similarity	NPD5275	Approved
0.5676	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7632	Discontinued
0.5673	Remote Similarity	NPD4753	Phase 2
0.567	Remote Similarity	NPD4271	Approved
0.567	Remote Similarity	NPD4268	Approved
0.5664	Remote Similarity	NPD5357	Phase 1
0.5652	Remote Similarity	NPD6373	Approved
0.5652	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6372	Approved
0.5648	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5221	Approved
0.5648	Remote Similarity	NPD5222	Approved
0.5644	Remote Similarity	NPD3668	Phase 3
0.5641	Remote Similarity	NPD6882	Approved
0.5641	Remote Similarity	NPD6053	Discontinued
0.5632	Remote Similarity	NPD1145	Discontinued
0.563	Remote Similarity	NPD2629	Approved
0.5619	Remote Similarity	NPD5785	Approved
0.5619	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.561	Remote Similarity	NPD5125	Phase 3
0.561	Remote Similarity	NPD5126	Approved
0.5607	Remote Similarity	NPD5282	Discontinued

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