NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	361.331
LogP:	1.93
LogD:	2.008
LogS:	-1.646
# Rotatable Bonds:	3
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	5.01
Fsp3:	0.9
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:	-4.855
MDCK Permeability:	5.907909326197114e-06
Pgp-inhibitor:	0.056
Pgp-substrate:	0.859
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.863
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.353
Plasma Protein Binding (PPB):	58.185550689697266%
Volume Distribution (VD):	0.824
Pgp-substrate:	29.526695251464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.914
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	9.154
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.453
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.32
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.265
Carcinogencity:	0.935
Eye Corrosion:	0.004
Eye Irritation:	0.057
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: NPC477925

Natural Product ID:	NPC477925
*Common Name:**	Ethenesulfonic acidDimethylamide
IUPAC Name:	1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol
Synonyms:
Standard InCHIKey:	NRYNTARIOIRWAB-PNJOJUOFSA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-17,21-24H,4-7,9-12H2,1-3H3/t14-,15-,16-,17?,18+,19+,20+/m1/s1
SMILES:	C[C@@]1(CC[C@@H]2C(=C1)CC[C@H]3[C@]2(C[C@@H](C[C@@]3(C)CO)O)C)C(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101353093
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2
Others	2

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	7.88	%	PMID[24997688]
NPT2	Others	Unspecified	IC50	>	10	ug/ml	PMID[24997688]
NPT2	Others	Unspecified	Inhibition	=	6.78	%	PMID[24997688]

☑ 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 NPC477925 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	180
0.1-0.2	1386
0.2-0.3	5433
0.3-0.4	15180
0.4-0.5	9176
0.5-0.6	5840
0.6-0.7	4077
0.7-0.8	1181
0.8-0.85	180
0.85-0.9	38
0.9-0.95	16
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC274079
0.9583	High Similarity	NPC477924
0.9577	High Similarity	NPC477923
0.9577	High Similarity	NPC66566
0.9306	High Similarity	NPC291503
0.92	High Similarity	NPC287749
0.9167	High Similarity	NPC243342
0.9167	High Similarity	NPC477138
0.9155	High Similarity	NPC242001
0.9054	High Similarity	NPC130136
0.9028	High Similarity	NPC471799
0.9014	High Similarity	NPC145498
0.8974	High Similarity	NPC238992
0.8933	High Similarity	NPC83351
0.8933	High Similarity	NPC167891
0.8904	High Similarity	NPC91858
0.8904	High Similarity	NPC471797
0.8846	High Similarity	NPC253402
0.8846	High Similarity	NPC159168
0.8831	High Similarity	NPC474531
0.8816	High Similarity	NPC328714
0.88	High Similarity	NPC471798
0.8767	High Similarity	NPC68443
0.8767	High Similarity	NPC182717
0.875	High Similarity	NPC237344
0.875	High Similarity	NPC92801
0.8734	High Similarity	NPC319238
0.8732	High Similarity	NPC208999
0.8718	High Similarity	NPC47763
0.8718	High Similarity	NPC30166
0.8701	High Similarity	NPC236112
0.8701	High Similarity	NPC96362
0.8684	High Similarity	NPC474989
0.8684	High Similarity	NPC22955
0.8684	High Similarity	NPC99168
0.8684	High Similarity	NPC300499
0.8684	High Similarity	NPC470396
0.8684	High Similarity	NPC476314
0.8667	High Similarity	NPC106432
0.8667	High Similarity	NPC321381
0.8667	High Similarity	NPC107059
0.8667	High Similarity	NPC321016
0.8649	High Similarity	NPC100334
0.8642	High Similarity	NPC477926
0.863	High Similarity	NPC167706
0.8608	High Similarity	NPC474634
0.8608	High Similarity	NPC207013
0.8608	High Similarity	NPC317458
0.859	High Similarity	NPC476646
0.8571	High Similarity	NPC53744
0.8571	High Similarity	NPC291379
0.8553	High Similarity	NPC91594
0.8553	High Similarity	NPC34177
0.8553	High Similarity	NPC472805
0.8553	High Similarity	NPC101475
0.8553	High Similarity	NPC90979
0.8553	High Similarity	NPC157996
0.8553	High Similarity	NPC40394
0.8553	High Similarity	NPC155986
0.8553	High Similarity	NPC198968
0.8553	High Similarity	NPC318495
0.8537	High Similarity	NPC474668
0.8533	High Similarity	NPC162742
0.8533	High Similarity	NPC288035
0.8533	High Similarity	NPC141071
0.8533	High Similarity	NPC230301
0.8533	High Similarity	NPC304309
0.8533	High Similarity	NPC285893
0.8533	High Similarity	NPC22105
0.8533	High Similarity	NPC257347
0.8533	High Similarity	NPC471723
0.8533	High Similarity	NPC28657
0.8533	High Similarity	NPC134847
0.8533	High Similarity	NPC136188
0.8519	High Similarity	NPC477604
0.85	High Similarity	NPC124172
0.85	High Similarity	NPC185568
0.8481	Intermediate Similarity	NPC212083
0.8481	Intermediate Similarity	NPC1272
0.8481	Intermediate Similarity	NPC470614
0.8462	Intermediate Similarity	NPC236237
0.8462	Intermediate Similarity	NPC322313
0.8462	Intermediate Similarity	NPC102253
0.8462	Intermediate Similarity	NPC13554
0.8442	Intermediate Similarity	NPC158662
0.8442	Intermediate Similarity	NPC275910
0.8442	Intermediate Similarity	NPC138621
0.8442	Intermediate Similarity	NPC6978
0.8442	Intermediate Similarity	NPC87604
0.8442	Intermediate Similarity	NPC253807
0.8442	Intermediate Similarity	NPC230295
0.8442	Intermediate Similarity	NPC473943
0.8442	Intermediate Similarity	NPC474216
0.8442	Intermediate Similarity	NPC477522
0.8442	Intermediate Similarity	NPC167037
0.8442	Intermediate Similarity	NPC196753
0.8442	Intermediate Similarity	NPC98386
0.8442	Intermediate Similarity	NPC244385
0.8434	Intermediate Similarity	NPC105495
0.8429	Intermediate Similarity	NPC290367
0.8421	Intermediate Similarity	NPC129165
0.8421	Intermediate Similarity	NPC30590
0.8421	Intermediate Similarity	NPC113733
0.8421	Intermediate Similarity	NPC265588
0.8421	Intermediate Similarity	NPC106364
0.8421	Intermediate Similarity	NPC27765
0.8421	Intermediate Similarity	NPC189883
0.8421	Intermediate Similarity	NPC253190
0.8421	Intermediate Similarity	NPC122418
0.8421	Intermediate Similarity	NPC300324
0.8421	Intermediate Similarity	NPC290598
0.8421	Intermediate Similarity	NPC240604
0.8421	Intermediate Similarity	NPC96319
0.8421	Intermediate Similarity	NPC120098
0.8421	Intermediate Similarity	NPC265328
0.8421	Intermediate Similarity	NPC134330
0.8415	Intermediate Similarity	NPC189777
0.8415	Intermediate Similarity	NPC470620
0.84	Intermediate Similarity	NPC306727
0.84	Intermediate Similarity	NPC469593
0.84	Intermediate Similarity	NPC469534
0.84	Intermediate Similarity	NPC469533
0.8395	Intermediate Similarity	NPC290731
0.8378	Intermediate Similarity	NPC242992
0.8378	Intermediate Similarity	NPC164022
0.8378	Intermediate Similarity	NPC110799
0.8375	Intermediate Similarity	NPC82538
0.8375	Intermediate Similarity	NPC237795
0.8354	Intermediate Similarity	NPC142163
0.8333	Intermediate Similarity	NPC30986
0.8333	Intermediate Similarity	NPC209430
0.8333	Intermediate Similarity	NPC80530
0.8333	Intermediate Similarity	NPC472463
0.8333	Intermediate Similarity	NPC143182
0.8333	Intermediate Similarity	NPC28862
0.8333	Intermediate Similarity	NPC100906
0.8333	Intermediate Similarity	NPC109546
0.8333	Intermediate Similarity	NPC47982
0.8333	Intermediate Similarity	NPC81306
0.8333	Intermediate Similarity	NPC197805
0.8333	Intermediate Similarity	NPC273410
0.8333	Intermediate Similarity	NPC84694
0.8333	Intermediate Similarity	NPC1319
0.8313	Intermediate Similarity	NPC67872
0.8312	Intermediate Similarity	NPC34019
0.8312	Intermediate Similarity	NPC470711
0.8312	Intermediate Similarity	NPC470758
0.8312	Intermediate Similarity	NPC214570
0.8293	Intermediate Similarity	NPC24277
0.8293	Intermediate Similarity	NPC94462
0.8289	Intermediate Similarity	NPC138374
0.8289	Intermediate Similarity	NPC34700
0.8272	Intermediate Similarity	NPC478102
0.8267	Intermediate Similarity	NPC474140
0.825	Intermediate Similarity	NPC248886
0.825	Intermediate Similarity	NPC101462
0.8243	Intermediate Similarity	NPC189745
0.8243	Intermediate Similarity	NPC34834
0.8235	Intermediate Similarity	NPC97404
0.8235	Intermediate Similarity	NPC41554
0.8228	Intermediate Similarity	NPC209944
0.8228	Intermediate Similarity	NPC164840
0.8228	Intermediate Similarity	NPC26117
0.8228	Intermediate Similarity	NPC295131
0.8228	Intermediate Similarity	NPC234193
0.8228	Intermediate Similarity	NPC22403
0.8228	Intermediate Similarity	NPC241290
0.8214	Intermediate Similarity	NPC259875
0.8214	Intermediate Similarity	NPC187785
0.8214	Intermediate Similarity	NPC470361
0.8214	Intermediate Similarity	NPC477606
0.8205	Intermediate Similarity	NPC72507
0.8205	Intermediate Similarity	NPC307965
0.8205	Intermediate Similarity	NPC285761
0.8205	Intermediate Similarity	NPC18603
0.8205	Intermediate Similarity	NPC76931
0.8194	Intermediate Similarity	NPC286669
0.8194	Intermediate Similarity	NPC222366
0.8194	Intermediate Similarity	NPC476039
0.8182	Intermediate Similarity	NPC470749
0.8182	Intermediate Similarity	NPC315261
0.8182	Intermediate Similarity	NPC202642
0.8182	Intermediate Similarity	NPC73875
0.8182	Intermediate Similarity	NPC470362
0.8182	Intermediate Similarity	NPC46160
0.8182	Intermediate Similarity	NPC237460
0.8169	Intermediate Similarity	NPC144650
0.8169	Intermediate Similarity	NPC225415
0.8158	Intermediate Similarity	NPC476366
0.8158	Intermediate Similarity	NPC201048
0.8148	Intermediate Similarity	NPC110778
0.8125	Intermediate Similarity	NPC474759
0.8125	Intermediate Similarity	NPC474752
0.8125	Intermediate Similarity	NPC209620
0.8125	Intermediate Similarity	NPC116202
0.8125	Intermediate Similarity	NPC474683
0.8125	Intermediate Similarity	NPC249423
0.8125	Intermediate Similarity	NPC6707
0.8125	Intermediate Similarity	NPC23852
0.8125	Intermediate Similarity	NPC474731

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 NPC477925 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1710
0.2-0.3	4046
0.3-0.4	2232
0.4-0.5	590
0.5-0.6	218
0.6-0.7	146
0.7-0.8	41
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
0.8533	High Similarity	NPD6942	Approved
0.8533	High Similarity	NPD7339	Approved
0.8462	Intermediate Similarity	NPD7525	Registered
0.8421	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7645	Phase 2
0.8182	Intermediate Similarity	NPD6933	Approved
0.7922	Intermediate Similarity	NPD6924	Approved
0.7922	Intermediate Similarity	NPD6926	Approved
0.7831	Intermediate Similarity	NPD4786	Approved
0.7821	Intermediate Similarity	NPD8264	Approved
0.7805	Intermediate Similarity	NPD3667	Approved
0.7778	Intermediate Similarity	NPD7509	Discontinued
0.7662	Intermediate Similarity	NPD7152	Approved
0.7662	Intermediate Similarity	NPD7150	Approved
0.7662	Intermediate Similarity	NPD7151	Approved
0.7632	Intermediate Similarity	NPD6923	Approved
0.7632	Intermediate Similarity	NPD6922	Approved
0.7532	Intermediate Similarity	NPD7143	Approved
0.7532	Intermediate Similarity	NPD7144	Approved
0.7468	Intermediate Similarity	NPD4784	Approved
0.7468	Intermediate Similarity	NPD4785	Approved
0.7442	Intermediate Similarity	NPD3618	Phase 1
0.7439	Intermediate Similarity	NPD6929	Approved
0.7436	Intermediate Similarity	NPD4243	Approved
0.7416	Intermediate Similarity	NPD7515	Phase 2
0.7412	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5328	Approved
0.7356	Intermediate Similarity	NPD7524	Approved
0.7356	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6931	Approved
0.7349	Intermediate Similarity	NPD4748	Discontinued
0.7349	Intermediate Similarity	NPD6930	Phase 2
0.7333	Intermediate Similarity	NPD6399	Phase 3
0.7294	Intermediate Similarity	NPD6695	Phase 3
0.7222	Intermediate Similarity	NPD6079	Approved
0.7209	Intermediate Similarity	NPD3668	Phase 3
0.7209	Intermediate Similarity	NPD3133	Approved
0.7209	Intermediate Similarity	NPD3666	Approved
0.7209	Intermediate Similarity	NPD3665	Phase 1
0.7195	Intermediate Similarity	NPD5776	Phase 2
0.7195	Intermediate Similarity	NPD6925	Approved
0.7195	Intermediate Similarity	NPD6932	Approved
0.7143	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7108	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7145	Approved
0.7065	Intermediate Similarity	NPD7748	Approved
0.7024	Intermediate Similarity	NPD6683	Phase 2
0.7021	Intermediate Similarity	NPD7902	Approved
0.7021	Intermediate Similarity	NPD4755	Approved
0.6966	Remote Similarity	NPD7750	Discontinued
0.6962	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4190	Phase 3
0.6951	Remote Similarity	NPD5275	Approved
0.6947	Remote Similarity	NPD4225	Approved
0.6941	Remote Similarity	NPD7332	Phase 2
0.6941	Remote Similarity	NPD7514	Phase 3
0.6932	Remote Similarity	NPD6893	Approved
0.6915	Remote Similarity	NPD4697	Phase 3
0.6915	Remote Similarity	NPD5221	Approved
0.6915	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.686	Remote Similarity	NPD6902	Approved
0.686	Remote Similarity	NPD6898	Phase 1
0.6854	Remote Similarity	NPD5279	Phase 3
0.6848	Remote Similarity	NPD6411	Approved
0.6842	Remote Similarity	NPD5173	Approved
0.6824	Remote Similarity	NPD4195	Approved
0.6813	Remote Similarity	NPD4753	Phase 2
0.6804	Remote Similarity	NPD5223	Approved
0.6771	Remote Similarity	NPD7638	Approved
0.6744	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4633	Approved
0.6735	Remote Similarity	NPD5224	Approved
0.6735	Remote Similarity	NPD5211	Phase 2
0.6735	Remote Similarity	NPD5225	Approved
0.6735	Remote Similarity	NPD5226	Approved
0.6711	Remote Similarity	NPD368	Approved
0.6702	Remote Similarity	NPD7900	Approved
0.6702	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7639	Approved
0.6701	Remote Similarity	NPD7640	Approved
0.67	Remote Similarity	NPD6402	Approved
0.67	Remote Similarity	NPD5739	Approved
0.67	Remote Similarity	NPD7128	Approved
0.67	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD6412	Phase 2
0.663	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6101	Approved
0.6602	Remote Similarity	NPD4634	Approved
0.66	Remote Similarity	NPD5141	Approved
0.6598	Remote Similarity	NPD5290	Discontinued
0.6591	Remote Similarity	NPD4221	Approved
0.6591	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD7320	Approved
0.6569	Remote Similarity	NPD6899	Approved
0.6556	Remote Similarity	NPD5329	Approved
0.6535	Remote Similarity	NPD4767	Approved
0.6535	Remote Similarity	NPD4768	Approved
0.6505	Remote Similarity	NPD6372	Approved
0.6505	Remote Similarity	NPD6373	Approved
0.6495	Remote Similarity	NPD6083	Phase 2
0.6495	Remote Similarity	NPD6084	Phase 2
0.6489	Remote Similarity	NPD8034	Phase 2
0.6489	Remote Similarity	NPD8035	Phase 2
0.6484	Remote Similarity	NPD7334	Approved
0.6484	Remote Similarity	NPD5330	Approved
0.6484	Remote Similarity	NPD7146	Approved
0.6484	Remote Similarity	NPD7521	Approved
0.6484	Remote Similarity	NPD6684	Approved
0.6484	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6409	Approved
0.6476	Remote Similarity	NPD8297	Approved
0.6471	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD5697	Approved
0.6465	Remote Similarity	NPD4159	Approved
0.6458	Remote Similarity	NPD5210	Approved
0.6458	Remote Similarity	NPD4629	Approved
0.6452	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6051	Approved
0.6444	Remote Similarity	NPD4197	Approved
0.6442	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD7290	Approved
0.6442	Remote Similarity	NPD7102	Approved
0.6415	Remote Similarity	NPD4632	Approved
0.6408	Remote Similarity	NPD4729	Approved
0.6408	Remote Similarity	NPD4730	Approved
0.6408	Remote Similarity	NPD5128	Approved
0.6408	Remote Similarity	NPD6686	Approved
0.6408	Remote Similarity	NPD6011	Approved
0.6389	Remote Similarity	NPD7115	Discovery
0.6383	Remote Similarity	NPD7136	Phase 2
0.6381	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD6617	Approved
0.6381	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6869	Approved
0.6381	Remote Similarity	NPD6650	Approved
0.6381	Remote Similarity	NPD8130	Phase 1
0.6381	Remote Similarity	NPD6649	Approved
0.6351	Remote Similarity	NPD342	Phase 1
0.6346	Remote Similarity	NPD6013	Approved
0.6346	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6014	Approved
0.6346	Remote Similarity	NPD6012	Approved
0.6344	Remote Similarity	NPD6672	Approved
0.6344	Remote Similarity	NPD5737	Approved
0.6344	Remote Similarity	NPD6903	Approved
0.6344	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4788	Approved
0.6322	Remote Similarity	NPD3617	Approved
0.6321	Remote Similarity	NPD6882	Approved
0.6316	Remote Similarity	NPD7637	Suspended
0.6304	Remote Similarity	NPD4693	Phase 3
0.6304	Remote Similarity	NPD4689	Approved
0.6304	Remote Similarity	NPD4690	Approved
0.6304	Remote Similarity	NPD4519	Discontinued
0.6304	Remote Similarity	NPD4623	Approved
0.6304	Remote Similarity	NPD4138	Approved
0.6304	Remote Similarity	NPD4688	Approved
0.6304	Remote Similarity	NPD5205	Approved
0.63	Remote Similarity	NPD5344	Discontinued
0.6286	Remote Similarity	NPD5247	Approved
0.6286	Remote Similarity	NPD5251	Approved
0.6286	Remote Similarity	NPD5250	Approved
0.6286	Remote Similarity	NPD5169	Approved
0.6286	Remote Similarity	NPD5248	Approved
0.6286	Remote Similarity	NPD5135	Approved
0.6286	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5249	Phase 3
0.6265	Remote Similarity	NPD4787	Phase 1
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5168	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6226	Remote Similarity	NPD5217	Approved
0.6226	Remote Similarity	NPD5216	Approved
0.6226	Remote Similarity	NPD5127	Approved
0.6226	Remote Similarity	NPD5215	Approved
0.6211	Remote Similarity	NPD3168	Discontinued
0.6207	Remote Similarity	NPD6116	Phase 1
0.619	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7327	Approved
0.6182	Remote Similarity	NPD7328	Approved
0.617	Remote Similarity	NPD4722	Approved
0.617	Remote Similarity	NPD4723	Approved
0.6161	Remote Similarity	NPD8033	Approved
0.6146	Remote Similarity	NPD5281	Approved
0.6146	Remote Similarity	NPD5284	Approved
0.6145	Remote Similarity	NPD3699	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data