NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.14
Volume:	281.368
LogP:	2.591
LogD:	1.813
LogS:	-3.076
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	4.16
Fsp3:	0.5
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:	-4.655
MDCK Permeability:	3.94604321627412e-05
Pgp-inhibitor:	0.475
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.832
30% Bioavailability (F30%):	0.11

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	89.47644805908203%
Volume Distribution (VD):	2.021
Pgp-substrate:	8.729674339294434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.541
CYP2C19-inhibitor:	0.803
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.574
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.716
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	9.143
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.517
Drug-inuced Liver Injury (DILI):	0.087
AMES Toxicity:	0.272
Rat Oral Acute Toxicity:	0.88
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.886
Carcinogencity:	0.892
Eye Corrosion:	0.168
Eye Irritation:	0.112
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: NPC40353

Natural Product ID:	NPC40353
*Common Name:**	Methyl 2-((2R,4As)-4A,8-Dimethyl-7-Oxo-1,2,3,4,4A,7-Hexahydronaphthalen-2-Yl)Acrylate
IUPAC Name:	methyl 2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4-tetrahydronaphthalen-2-yl]prop-2-enoate
Synonyms:
Standard InCHIKey:	DRRPONQYYUWLRC-WBMJQRKESA-N
Standard InCHI:	InChI=1S/C16H20O3/c1-10(15(18)19-4)12-5-7-16(3)8-6-14(17)11(2)13(16)9-12/h6,8,12H,1,5,7,9H2,2-4H3/t12-,16+/m1/s1
SMILES:	C=C([C@@H]1CC[C@@]2(C)C=CC(=O)C(=C2C1)C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087216
PubChem CID:	14864224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17944538]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22823026]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	leaves and stems	Ha Long, Quang Ninh province, Vietnam	2014-Jul	PMID[25769817]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29792702]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14254	Kandelia candel	Species	Rhizophoraceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	Inhibition	=	29.0	%	PMID[550126]

☑ 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 NPC40353 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	183
0.1-0.2	1186
0.2-0.3	5499
0.3-0.4	14791
0.4-0.5	9759
0.5-0.6	6815
0.6-0.7	3804
0.7-0.8	623
0.8-0.85	31
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8625	High Similarity	NPC189311
0.8553	High Similarity	NPC472300
0.8533	High Similarity	NPC65650
0.8442	Intermediate Similarity	NPC471220
0.84	Intermediate Similarity	NPC20025
0.8395	Intermediate Similarity	NPC177932
0.8313	Intermediate Similarity	NPC215831
0.8293	Intermediate Similarity	NPC220478
0.8214	Intermediate Similarity	NPC284561
0.8214	Intermediate Similarity	NPC73995
0.8214	Intermediate Similarity	NPC5509
0.8193	Intermediate Similarity	NPC477228
0.8182	Intermediate Similarity	NPC27205
0.8182	Intermediate Similarity	NPC473223
0.8182	Intermediate Similarity	NPC180886
0.8148	Intermediate Similarity	NPC118423
0.8148	Intermediate Similarity	NPC22611
0.8148	Intermediate Similarity	NPC193198
0.8101	Intermediate Similarity	NPC150646
0.8095	Intermediate Similarity	NPC226863
0.8077	Intermediate Similarity	NPC97377
0.8052	Intermediate Similarity	NPC244166
0.8052	Intermediate Similarity	NPC476346
0.8049	Intermediate Similarity	NPC475100
0.8049	Intermediate Similarity	NPC30486
0.8049	Intermediate Similarity	NPC149869
0.8025	Intermediate Similarity	NPC200513
0.8025	Intermediate Similarity	NPC178676
0.8025	Intermediate Similarity	NPC100297
0.8025	Intermediate Similarity	NPC186276
0.8025	Intermediate Similarity	NPC268122
0.7976	Intermediate Similarity	NPC181327
0.7975	Intermediate Similarity	NPC74410
0.7952	Intermediate Similarity	NPC110405
0.7927	Intermediate Similarity	NPC474976
0.7927	Intermediate Similarity	NPC474790
0.7922	Intermediate Similarity	NPC166797
0.7907	Intermediate Similarity	NPC476369
0.7907	Intermediate Similarity	NPC152467
0.7907	Intermediate Similarity	NPC476437
0.7901	Intermediate Similarity	NPC282293
0.7901	Intermediate Similarity	NPC40228
0.7901	Intermediate Similarity	NPC149237
0.7901	Intermediate Similarity	NPC278459
0.7882	Intermediate Similarity	NPC472302
0.7875	Intermediate Similarity	NPC469690
0.7857	Intermediate Similarity	NPC168248
0.7848	Intermediate Similarity	NPC41780
0.7848	Intermediate Similarity	NPC316500
0.7848	Intermediate Similarity	NPC187568
0.7848	Intermediate Similarity	NPC165711
0.7841	Intermediate Similarity	NPC477130
0.7841	Intermediate Similarity	NPC477129
0.7841	Intermediate Similarity	NPC38830
0.7841	Intermediate Similarity	NPC470697
0.7831	Intermediate Similarity	NPC474359
0.7821	Intermediate Similarity	NPC476795
0.7821	Intermediate Similarity	NPC228978
0.7816	Intermediate Similarity	NPC473944
0.7816	Intermediate Similarity	NPC303697
0.7808	Intermediate Similarity	NPC251118
0.7805	Intermediate Similarity	NPC321289
0.7805	Intermediate Similarity	NPC327969
0.7805	Intermediate Similarity	NPC302661
0.7805	Intermediate Similarity	NPC94200
0.7805	Intermediate Similarity	NPC238991
0.7792	Intermediate Similarity	NPC276336
0.7792	Intermediate Similarity	NPC56747
0.7792	Intermediate Similarity	NPC109576
0.7792	Intermediate Similarity	NPC180015
0.7792	Intermediate Similarity	NPC130016
0.7791	Intermediate Similarity	NPC36668
0.7791	Intermediate Similarity	NPC118011
0.7791	Intermediate Similarity	NPC173042
0.7778	Intermediate Similarity	NPC267517
0.7778	Intermediate Similarity	NPC195424
0.7778	Intermediate Similarity	NPC26139
0.7765	Intermediate Similarity	NPC30421
0.7753	Intermediate Similarity	NPC171395
0.7753	Intermediate Similarity	NPC295347
0.775	Intermediate Similarity	NPC128276
0.775	Intermediate Similarity	NPC471409
0.775	Intermediate Similarity	NPC321514
0.775	Intermediate Similarity	NPC275494
0.775	Intermediate Similarity	NPC179028
0.7738	Intermediate Similarity	NPC474537
0.7738	Intermediate Similarity	NPC474680
0.7738	Intermediate Similarity	NPC65661
0.7738	Intermediate Similarity	NPC86316
0.7738	Intermediate Similarity	NPC323765
0.7738	Intermediate Similarity	NPC29447
0.7738	Intermediate Similarity	NPC106416
0.7733	Intermediate Similarity	NPC188292
0.7733	Intermediate Similarity	NPC260474
0.7727	Intermediate Similarity	NPC115021
0.7727	Intermediate Similarity	NPC475657
0.7722	Intermediate Similarity	NPC899
0.7711	Intermediate Similarity	NPC49019
0.7701	Intermediate Similarity	NPC8062
0.7701	Intermediate Similarity	NPC51486
0.7701	Intermediate Similarity	NPC212679
0.7701	Intermediate Similarity	NPC220454
0.7701	Intermediate Similarity	NPC469372
0.7701	Intermediate Similarity	NPC469595
0.7701	Intermediate Similarity	NPC101651
0.7701	Intermediate Similarity	NPC159748
0.7692	Intermediate Similarity	NPC476046
0.7692	Intermediate Similarity	NPC251970
0.7692	Intermediate Similarity	NPC241854
0.7692	Intermediate Similarity	NPC306928
0.7683	Intermediate Similarity	NPC474955
0.7683	Intermediate Similarity	NPC475665
0.7683	Intermediate Similarity	NPC471898
0.7683	Intermediate Similarity	NPC477372
0.7683	Intermediate Similarity	NPC474085
0.7683	Intermediate Similarity	NPC90055
0.7674	Intermediate Similarity	NPC477128
0.7662	Intermediate Similarity	NPC160817
0.7662	Intermediate Similarity	NPC257618
0.7654	Intermediate Similarity	NPC190211
0.7654	Intermediate Similarity	NPC264227
0.7654	Intermediate Similarity	NPC263951
0.7654	Intermediate Similarity	NPC63649
0.7654	Intermediate Similarity	NPC469620
0.7654	Intermediate Similarity	NPC472965
0.7654	Intermediate Similarity	NPC476177
0.7654	Intermediate Similarity	NPC471299
0.7647	Intermediate Similarity	NPC195640
0.7647	Intermediate Similarity	NPC472863
0.764	Intermediate Similarity	NPC476415
0.7632	Intermediate Similarity	NPC265574
0.7625	Intermediate Similarity	NPC180290
0.7625	Intermediate Similarity	NPC57744
0.7619	Intermediate Similarity	NPC238197
0.7619	Intermediate Similarity	NPC320801
0.7614	Intermediate Similarity	NPC474018
0.7614	Intermediate Similarity	NPC473986
0.7614	Intermediate Similarity	NPC218301
0.7614	Intermediate Similarity	NPC65513
0.7595	Intermediate Similarity	NPC279666
0.7595	Intermediate Similarity	NPC155587
0.7595	Intermediate Similarity	NPC138408
0.7595	Intermediate Similarity	NPC193351
0.7595	Intermediate Similarity	NPC226669
0.7595	Intermediate Similarity	NPC192540
0.759	Intermediate Similarity	NPC320514
0.759	Intermediate Similarity	NPC240302
0.759	Intermediate Similarity	NPC85772
0.759	Intermediate Similarity	NPC142683
0.7586	Intermediate Similarity	NPC469546
0.7586	Intermediate Similarity	NPC168131
0.7586	Intermediate Similarity	NPC262043
0.7586	Intermediate Similarity	NPC285982
0.7586	Intermediate Similarity	NPC280833
0.7586	Intermediate Similarity	NPC174342
0.7586	Intermediate Similarity	NPC177141
0.7582	Intermediate Similarity	NPC84335
0.7582	Intermediate Similarity	NPC208094
0.7582	Intermediate Similarity	NPC38530
0.7564	Intermediate Similarity	NPC35656
0.7564	Intermediate Similarity	NPC470237
0.7561	Intermediate Similarity	NPC47747
0.7561	Intermediate Similarity	NPC476809
0.7561	Intermediate Similarity	NPC474956
0.7558	Intermediate Similarity	NPC478144
0.7558	Intermediate Similarity	NPC312561
0.7558	Intermediate Similarity	NPC478145
0.7556	Intermediate Similarity	NPC209355
0.7556	Intermediate Similarity	NPC33473
0.7532	Intermediate Similarity	NPC469660
0.7531	Intermediate Similarity	NPC198240
0.7531	Intermediate Similarity	NPC169095
0.7531	Intermediate Similarity	NPC62336
0.7531	Intermediate Similarity	NPC478246
0.7531	Intermediate Similarity	NPC105197
0.7531	Intermediate Similarity	NPC469996
0.7531	Intermediate Similarity	NPC4827
0.7531	Intermediate Similarity	NPC478247
0.7531	Intermediate Similarity	NPC59436
0.7531	Intermediate Similarity	NPC189485
0.7529	Intermediate Similarity	NPC161957
0.7529	Intermediate Similarity	NPC21471
0.7529	Intermediate Similarity	NPC476426
0.7529	Intermediate Similarity	NPC33570
0.7529	Intermediate Similarity	NPC2709
0.7528	Intermediate Similarity	NPC472871
0.7527	Intermediate Similarity	NPC310981
0.75	Intermediate Similarity	NPC474842
0.75	Intermediate Similarity	NPC476614
0.75	Intermediate Similarity	NPC198818
0.75	Intermediate Similarity	NPC41017
0.75	Intermediate Similarity	NPC263582
0.75	Intermediate Similarity	NPC266119
0.75	Intermediate Similarity	NPC475965
0.75	Intermediate Similarity	NPC108368
0.75	Intermediate Similarity	NPC57079
0.75	Intermediate Similarity	NPC222358
0.75	Intermediate Similarity	NPC102197
0.75	Intermediate Similarity	NPC155198
0.75	Intermediate Similarity	NPC218477

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 NPC40353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1472
0.2-0.3	3972
0.3-0.4	2371
0.4-0.5	715
0.5-0.6	277
0.6-0.7	150
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8395	Intermediate Similarity	NPD1694	Approved
0.8025	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8039	Approved
0.7765	Intermediate Similarity	NPD3573	Approved
0.7647	Intermediate Similarity	NPD5330	Approved
0.7647	Intermediate Similarity	NPD6684	Approved
0.7647	Intermediate Similarity	NPD7146	Approved
0.7647	Intermediate Similarity	NPD7521	Approved
0.7647	Intermediate Similarity	NPD7334	Approved
0.7647	Intermediate Similarity	NPD6409	Approved
0.7614	Intermediate Similarity	NPD5693	Phase 1
0.7471	Intermediate Similarity	NPD5737	Approved
0.7471	Intermediate Similarity	NPD6672	Approved
0.7471	Intermediate Similarity	NPD6903	Approved
0.7471	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4691	Approved
0.7303	Intermediate Similarity	NPD5207	Approved
0.7273	Intermediate Similarity	NPD5208	Approved
0.725	Intermediate Similarity	NPD4058	Approved
0.7222	Intermediate Similarity	NPD5694	Approved
0.7191	Intermediate Similarity	NPD6673	Approved
0.7191	Intermediate Similarity	NPD6904	Approved
0.7191	Intermediate Similarity	NPD6080	Approved
0.7179	Intermediate Similarity	NPD4137	Phase 3
0.7176	Intermediate Similarity	NPD5209	Approved
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7111	Intermediate Similarity	NPD5785	Approved
0.7111	Intermediate Similarity	NPD5692	Phase 3
0.7089	Intermediate Similarity	NPD4747	Approved
0.7065	Intermediate Similarity	NPD7900	Approved
0.7065	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7748	Approved
0.7045	Intermediate Similarity	NPD4623	Approved
0.7045	Intermediate Similarity	NPD6098	Approved
0.7045	Intermediate Similarity	NPD4519	Discontinued
0.7045	Intermediate Similarity	NPD5690	Phase 2
0.7037	Intermediate Similarity	NPD4687	Approved
0.7033	Intermediate Similarity	NPD7515	Phase 2
0.7033	Intermediate Similarity	NPD6050	Approved
0.7033	Intermediate Similarity	NPD5284	Approved
0.7033	Intermediate Similarity	NPD5281	Approved
0.7013	Intermediate Similarity	NPD7331	Phase 2
0.7013	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3666	Approved
0.7011	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD3665	Phase 1
0.6989	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5695	Phase 3
0.6977	Remote Similarity	NPD4223	Phase 3
0.6977	Remote Similarity	NPD4221	Approved
0.6915	Remote Similarity	NPD7732	Phase 3
0.6883	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6001	Approved
0.6854	Remote Similarity	NPD3618	Phase 1
0.6848	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD6084	Phase 2
0.6842	Remote Similarity	NPD6083	Phase 2
0.6842	Remote Similarity	NPD7902	Approved
0.6829	Remote Similarity	NPD5733	Approved
0.6818	Remote Similarity	NPD4197	Approved
0.6813	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5276	Approved
0.6786	Remote Similarity	NPD4756	Discovery
0.6782	Remote Similarity	NPD3667	Approved
0.6774	Remote Similarity	NPD6399	Phase 3
0.6771	Remote Similarity	NPD5696	Approved
0.6753	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5329	Approved
0.6706	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6634	Remote Similarity	NPD5697	Approved
0.6632	Remote Similarity	NPD5654	Approved
0.6632	Remote Similarity	NPD4629	Approved
0.6632	Remote Similarity	NPD5210	Approved
0.663	Remote Similarity	NPD5328	Approved
0.663	Remote Similarity	NPD4753	Phase 2
0.6629	Remote Similarity	NPD4786	Approved
0.6629	Remote Similarity	NPD3668	Phase 3
0.6628	Remote Similarity	NPD4195	Approved
0.6625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7638	Approved
0.6569	Remote Similarity	NPD6011	Approved
0.6569	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD6899	Approved
0.6562	Remote Similarity	NPD5222	Approved
0.6562	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7614	Phase 1
0.6562	Remote Similarity	NPD5221	Approved
0.6559	Remote Similarity	NPD6698	Approved
0.6559	Remote Similarity	NPD46	Approved
0.6556	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5363	Approved
0.6542	Remote Similarity	NPD7115	Discovery
0.6533	Remote Similarity	NPD287	Approved
0.6531	Remote Similarity	NPD7640	Approved
0.6531	Remote Similarity	NPD7639	Approved
0.6517	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6013	Approved
0.6505	Remote Similarity	NPD6014	Approved
0.6505	Remote Similarity	NPD6012	Approved
0.6495	Remote Similarity	NPD5959	Approved
0.6495	Remote Similarity	NPD5173	Approved
0.6494	Remote Similarity	NPD4194	Approved
0.6494	Remote Similarity	NPD4191	Approved
0.6494	Remote Similarity	NPD4192	Approved
0.6494	Remote Similarity	NPD4193	Approved
0.6489	Remote Similarity	NPD6411	Approved
0.6479	Remote Similarity	NPD28	Approved
0.6479	Remote Similarity	NPD29	Approved
0.6471	Remote Similarity	NPD6614	Approved
0.6452	Remote Similarity	NPD6051	Approved
0.6442	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD7290	Approved
0.6442	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD4225	Approved
0.6421	Remote Similarity	NPD4202	Approved
0.641	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6686	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.6381	Remote Similarity	NPD6650	Approved
0.6381	Remote Similarity	NPD8130	Phase 1
0.6381	Remote Similarity	NPD6649	Approved
0.6381	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD6869	Approved
0.6381	Remote Similarity	NPD6617	Approved
0.6373	Remote Similarity	NPD7128	Approved
0.6373	Remote Similarity	NPD5739	Approved
0.6373	Remote Similarity	NPD6402	Approved
0.6373	Remote Similarity	NPD6008	Approved
0.6373	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6404	Discontinued
0.6364	Remote Similarity	NPD5285	Approved
0.6364	Remote Similarity	NPD5286	Approved
0.6354	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4518	Approved
0.6337	Remote Similarity	NPD6052	Approved
0.6333	Remote Similarity	NPD5362	Discontinued
0.6333	Remote Similarity	NPD7154	Phase 3
0.6321	Remote Similarity	NPD6882	Approved
0.6321	Remote Similarity	NPD8297	Approved
0.6311	Remote Similarity	NPD5701	Approved
0.6301	Remote Similarity	NPD3172	Approved
0.63	Remote Similarity	NPD5223	Approved
0.6292	Remote Similarity	NPD8028	Phase 2
0.6292	Remote Similarity	NPD5369	Approved
0.6277	Remote Similarity	NPD6101	Approved
0.6277	Remote Similarity	NPD1695	Approved
0.6277	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5141	Approved
0.6264	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD5778	Approved
0.625	Remote Similarity	NPD5779	Approved
0.6238	Remote Similarity	NPD5224	Approved
0.6238	Remote Similarity	NPD4633	Approved
0.6238	Remote Similarity	NPD5226	Approved
0.6238	Remote Similarity	NPD5225	Approved
0.6224	Remote Similarity	NPD4697	Phase 3
0.6222	Remote Similarity	NPD4269	Approved
0.6222	Remote Similarity	NPD6435	Approved
0.6222	Remote Similarity	NPD4270	Approved
0.6216	Remote Similarity	NPD3194	Approved
0.6216	Remote Similarity	NPD3195	Phase 2
0.6216	Remote Similarity	NPD3196	Approved
0.6216	Remote Similarity	NPD4266	Approved
0.6211	Remote Similarity	NPD4096	Approved
0.62	Remote Similarity	NPD2066	Phase 3
0.619	Remote Similarity	NPD6373	Approved
0.619	Remote Similarity	NPD6372	Approved
0.618	Remote Similarity	NPD5368	Approved
0.6176	Remote Similarity	NPD5175	Approved
0.6176	Remote Similarity	NPD5174	Approved
0.6162	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4788	Approved
0.6147	Remote Similarity	NPD6868	Approved
0.6129	Remote Similarity	NPD6422	Discontinued
0.6129	Remote Similarity	NPD5786	Approved
0.6117	Remote Similarity	NPD5909	Discontinued
0.6111	Remote Similarity	NPD4692	Approved
0.6111	Remote Similarity	NPD4139	Approved
0.6111	Remote Similarity	NPD7094	Approved
0.6111	Remote Similarity	NPD6858	Approved
0.61	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6317	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