NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	352.775
LogP:	1.709
LogD:	2.099
LogS:	-2.79
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	5.814
Fsp3:	0.95
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:	-5.801
MDCK Permeability:	1.09984575829003e-05
Pgp-inhibitor:	0.54
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	80.520751953125%
Volume Distribution (VD):	0.514
Pgp-substrate:	9.45167064666748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.707
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.292
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	2.46
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.574
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.519
Skin Sensitization:	0.925
Carcinogencity:	0.457
Eye Corrosion:	0.064
Eye Irritation:	0.387
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC477930

Natural Product ID:	NPC477930
*Common Name:**	(1S,4S,5R,9S,10R,13S,14R)-5,14-bis(hydroxymethyl)-9-methyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
IUPAC Name:	(1S,4S,5R,9S,10R,13S,14R)-5,14-bis(hydroxymethyl)-9-methyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
Synonyms:
Standard InCHIKey:	UUBNGVXGDKXQQJ-YNZDMMAESA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-18-6-2-7-20(12-22,17(23)24)16(18)5-8-19-9-13(3-4-15(18)19)14(10-19)11-21/h13-16,21-22H,2-12H2,1H3,(H,23,24)/t13-,14-,15-,16-,18-,19-,20-/m0/s1
SMILES:	C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@@H](C3)[C@@H](C4)CO)(CO)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118708062
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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	=	7.81	%	PMID[24997688]
NPT2	Others	Unspecified	IC50	>	10	ug/ml	PMID[24997688]
NPT2	Others	Unspecified	Inhibition	=	15.69	%	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 NPC477930 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	300
0.1-0.2	3278
0.2-0.3	13716
0.3-0.4	10274
0.4-0.5	6020
0.5-0.6	5589
0.6-0.7	2786
0.7-0.8	596
0.8-0.85	82
0.85-0.9	34
0.9-0.95	18
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC477932
0.9714	High Similarity	NPC477933
0.9571	High Similarity	NPC477934
0.9412	High Similarity	NPC319671
0.9412	High Similarity	NPC476734
0.9412	High Similarity	NPC469941
0.9412	High Similarity	NPC252032
0.9306	High Similarity	NPC477918
0.9275	High Similarity	NPC477929
0.9143	High Similarity	NPC469940
0.9	High Similarity	NPC477850
0.8971	High Similarity	NPC477931
0.8971	High Similarity	NPC268736
0.8971	High Similarity	NPC42060
0.8947	High Similarity	NPC477935
0.8904	High Similarity	NPC4209
0.8889	High Similarity	NPC280026
0.8889	High Similarity	NPC167702
0.8857	High Similarity	NPC64466
0.8784	High Similarity	NPC180199
0.8784	High Similarity	NPC317913
0.8784	High Similarity	NPC207010
0.8784	High Similarity	NPC477919
0.8767	High Similarity	NPC472311
0.8767	High Similarity	NPC212733
0.8701	High Similarity	NPC477936
0.8667	High Similarity	NPC185465
0.8667	High Similarity	NPC476732
0.8667	High Similarity	NPC199965
0.8667	High Similarity	NPC34046
0.8667	High Similarity	NPC171426
0.8667	High Similarity	NPC224802
0.8667	High Similarity	NPC80089
0.8667	High Similarity	NPC324700
0.8611	High Similarity	NPC473267
0.8571	High Similarity	NPC130459
0.8571	High Similarity	NPC474221
0.8571	High Similarity	NPC478180
0.8553	High Similarity	NPC201276
0.8553	High Similarity	NPC80891
0.8553	High Similarity	NPC320144
0.8553	High Similarity	NPC52951
0.8533	High Similarity	NPC298168
0.8533	High Similarity	NPC143133
0.85	High Similarity	NPC302111
0.8481	Intermediate Similarity	NPC319909
0.8481	Intermediate Similarity	NPC473336
0.8481	Intermediate Similarity	NPC471044
0.8472	Intermediate Similarity	NPC108131
0.8472	Intermediate Similarity	NPC476731
0.8421	Intermediate Similarity	NPC329117
0.8395	Intermediate Similarity	NPC252714
0.8395	Intermediate Similarity	NPC134197
0.8375	Intermediate Similarity	NPC201655
0.8356	Intermediate Similarity	NPC58057
0.8356	Intermediate Similarity	NPC156277
0.8356	Intermediate Similarity	NPC320549
0.8356	Intermediate Similarity	NPC151018
0.8333	Intermediate Similarity	NPC196197
0.8333	Intermediate Similarity	NPC474962
0.8333	Intermediate Similarity	NPC12933
0.8293	Intermediate Similarity	NPC183374
0.8293	Intermediate Similarity	NPC211162
0.8289	Intermediate Similarity	NPC264602
0.8243	Intermediate Similarity	NPC310766
0.8243	Intermediate Similarity	NPC232112
0.8228	Intermediate Similarity	NPC121121
0.8228	Intermediate Similarity	NPC61107
0.8228	Intermediate Similarity	NPC30583
0.8228	Intermediate Similarity	NPC289486
0.8205	Intermediate Similarity	NPC472853
0.8205	Intermediate Similarity	NPC261616
0.8193	Intermediate Similarity	NPC56962
0.8193	Intermediate Similarity	NPC57954
0.8193	Intermediate Similarity	NPC24705
0.8193	Intermediate Similarity	NPC213832
0.8158	Intermediate Similarity	NPC246445
0.8133	Intermediate Similarity	NPC472854
0.8133	Intermediate Similarity	NPC254340
0.8125	Intermediate Similarity	NPC259173
0.8125	Intermediate Similarity	NPC15821
0.8108	Intermediate Similarity	NPC472309
0.8101	Intermediate Similarity	NPC58631
0.8082	Intermediate Similarity	NPC321732
0.8082	Intermediate Similarity	NPC327728
0.8082	Intermediate Similarity	NPC6120
0.8082	Intermediate Similarity	NPC131892
0.8082	Intermediate Similarity	NPC213178
0.8082	Intermediate Similarity	NPC324607
0.8077	Intermediate Similarity	NPC472310
0.8072	Intermediate Similarity	NPC471900
0.8072	Intermediate Similarity	NPC146937
0.8052	Intermediate Similarity	NPC474404
0.8052	Intermediate Similarity	NPC471151
0.8049	Intermediate Similarity	NPC92139
0.8049	Intermediate Similarity	NPC80590
0.8026	Intermediate Similarity	NPC132064
0.8026	Intermediate Similarity	NPC179858
0.8026	Intermediate Similarity	NPC21220
0.8026	Intermediate Similarity	NPC97534
0.8026	Intermediate Similarity	NPC195155
0.8026	Intermediate Similarity	NPC24014
0.8026	Intermediate Similarity	NPC273366
0.8026	Intermediate Similarity	NPC125767
0.8026	Intermediate Similarity	NPC27349
0.8026	Intermediate Similarity	NPC174964
0.8025	Intermediate Similarity	NPC50438
0.8	Intermediate Similarity	NPC13494
0.7976	Intermediate Similarity	NPC116146
0.7976	Intermediate Similarity	NPC24772
0.7975	Intermediate Similarity	NPC477851
0.7952	Intermediate Similarity	NPC96496
0.7952	Intermediate Similarity	NPC269360
0.7952	Intermediate Similarity	NPC264005
0.7945	Intermediate Similarity	NPC473225
0.7941	Intermediate Similarity	NPC476735
0.7922	Intermediate Similarity	NPC472487
0.7922	Intermediate Similarity	NPC5767
0.7922	Intermediate Similarity	NPC472486
0.7922	Intermediate Similarity	NPC475742
0.7907	Intermediate Similarity	NPC476189
0.7907	Intermediate Similarity	NPC471902
0.7907	Intermediate Similarity	NPC473690
0.7907	Intermediate Similarity	NPC287118
0.7901	Intermediate Similarity	NPC292458
0.7901	Intermediate Similarity	NPC268578
0.7901	Intermediate Similarity	NPC217559
0.7901	Intermediate Similarity	NPC245866
0.7882	Intermediate Similarity	NPC169933
0.7867	Intermediate Similarity	NPC89310
0.7831	Intermediate Similarity	NPC2783
0.7831	Intermediate Similarity	NPC472272
0.7831	Intermediate Similarity	NPC70661
0.7821	Intermediate Similarity	NPC169389
0.7821	Intermediate Similarity	NPC475031
0.7821	Intermediate Similarity	NPC68828
0.7821	Intermediate Similarity	NPC66105
0.7821	Intermediate Similarity	NPC23884
0.7821	Intermediate Similarity	NPC221420
0.7816	Intermediate Similarity	NPC206878
0.7791	Intermediate Similarity	NPC475416
0.7791	Intermediate Similarity	NPC471901
0.7778	Intermediate Similarity	NPC242771
0.7778	Intermediate Similarity	NPC311642
0.7778	Intermediate Similarity	NPC164289
0.7778	Intermediate Similarity	NPC328007
0.7778	Intermediate Similarity	NPC100366
0.7778	Intermediate Similarity	NPC317066
0.7763	Intermediate Similarity	NPC161187
0.7763	Intermediate Similarity	NPC330659
0.7763	Intermediate Similarity	NPC244708
0.775	Intermediate Similarity	NPC470609
0.7738	Intermediate Similarity	NPC33768
0.7738	Intermediate Similarity	NPC263802
0.7727	Intermediate Similarity	NPC263135
0.7727	Intermediate Similarity	NPC288906
0.7727	Intermediate Similarity	NPC266431
0.7727	Intermediate Similarity	NPC62407
0.7727	Intermediate Similarity	NPC205173
0.7727	Intermediate Similarity	NPC287354
0.7722	Intermediate Similarity	NPC472608
0.7722	Intermediate Similarity	NPC26029
0.7711	Intermediate Similarity	NPC473350
0.7711	Intermediate Similarity	NPC131350
0.7711	Intermediate Similarity	NPC264317
0.7711	Intermediate Similarity	NPC294438
0.7703	Intermediate Similarity	NPC470956
0.7703	Intermediate Similarity	NPC469724
0.7703	Intermediate Similarity	NPC281203
0.7703	Intermediate Similarity	NPC2568
0.7703	Intermediate Similarity	NPC103647
0.7703	Intermediate Similarity	NPC474954
0.7703	Intermediate Similarity	NPC260319
0.7703	Intermediate Similarity	NPC180777
0.7703	Intermediate Similarity	NPC100917
0.7703	Intermediate Similarity	NPC31187
0.7692	Intermediate Similarity	NPC474020
0.7692	Intermediate Similarity	NPC471046
0.7683	Intermediate Similarity	NPC471037
0.7683	Intermediate Similarity	NPC472744
0.7683	Intermediate Similarity	NPC327451
0.7662	Intermediate Similarity	NPC317212
0.7662	Intermediate Similarity	NPC472945
0.7662	Intermediate Similarity	NPC133922
0.7662	Intermediate Similarity	NPC472944
0.7654	Intermediate Similarity	NPC469745
0.7647	Intermediate Similarity	NPC474719
0.7647	Intermediate Similarity	NPC16377
0.764	Intermediate Similarity	NPC234564
0.764	Intermediate Similarity	NPC116683
0.7632	Intermediate Similarity	NPC197701
0.7632	Intermediate Similarity	NPC478227
0.7625	Intermediate Similarity	NPC192744
0.7625	Intermediate Similarity	NPC201459
0.7619	Intermediate Similarity	NPC12774
0.7619	Intermediate Similarity	NPC83242
0.7595	Intermediate Similarity	NPC171658
0.759	Intermediate Similarity	NPC263974
0.759	Intermediate Similarity	NPC219535
0.759	Intermediate Similarity	NPC473299

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 NPC477930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	3454
0.2-0.3	3618
0.3-0.4	1033
0.4-0.5	303
0.5-0.6	253
0.6-0.7	123
0.7-0.8	9
0.8-0.85	11
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD6117	Approved
0.8889	High Similarity	NPD6113	Clinical (unspecified phase)
0.8784	High Similarity	NPD6116	Phase 1
0.8667	High Similarity	NPD6114	Approved
0.8667	High Similarity	NPD6115	Approved
0.8667	High Similarity	NPD6697	Approved
0.8667	High Similarity	NPD6118	Approved
0.8611	High Similarity	NPD6081	Approved
0.8472	Intermediate Similarity	NPD4789	Approved
0.8429	Intermediate Similarity	NPD4224	Phase 2
0.8356	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD4245	Approved
0.8219	Intermediate Similarity	NPD4244	Approved
0.8082	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD3698	Phase 2
0.8082	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3702	Approved
0.7945	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD5360	Phase 3
0.7867	Intermediate Similarity	NPD5777	Approved
0.7711	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3703	Phase 2
0.7403	Intermediate Similarity	NPD4758	Discontinued
0.7368	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5364	Discontinued
0.7284	Intermediate Similarity	NPD3671	Phase 1
0.7262	Intermediate Similarity	NPD4788	Approved
0.7191	Intermediate Similarity	NPD8034	Phase 2
0.7191	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD3198	Approved
0.6989	Remote Similarity	NPD6083	Phase 2
0.6989	Remote Similarity	NPD6084	Phase 2
0.6977	Remote Similarity	NPD4786	Approved
0.6923	Remote Similarity	NPD6399	Phase 3
0.6857	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8418	Phase 2
0.6835	Remote Similarity	NPD4787	Phase 1
0.6778	Remote Similarity	NPD4753	Phase 2
0.6744	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.663	Remote Similarity	NPD7515	Phase 2
0.6596	Remote Similarity	NPD5695	Phase 3
0.6593	Remote Similarity	NPD5328	Approved
0.6591	Remote Similarity	NPD3666	Approved
0.6591	Remote Similarity	NPD3665	Phase 1
0.6591	Remote Similarity	NPD3133	Approved
0.6582	Remote Similarity	NPD6705	Phase 1
0.6562	Remote Similarity	NPD5696	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4802	Phase 2
0.6471	Remote Similarity	NPD3617	Approved
0.6471	Remote Similarity	NPD4238	Approved
0.6452	Remote Similarity	NPD6079	Approved
0.6444	Remote Similarity	NPD7334	Approved
0.6444	Remote Similarity	NPD6409	Approved
0.6444	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5330	Approved
0.6444	Remote Similarity	NPD3618	Phase 1
0.6444	Remote Similarity	NPD7146	Approved
0.6444	Remote Similarity	NPD7521	Approved
0.6444	Remote Similarity	NPD6684	Approved
0.6421	Remote Similarity	NPD4629	Approved
0.6421	Remote Similarity	NPD5210	Approved
0.64	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7638	Approved
0.6389	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6899	Approved
0.6373	Remote Similarity	NPD7320	Approved
0.6373	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD4223	Phase 3
0.6364	Remote Similarity	NPD4221	Approved
0.6333	Remote Similarity	NPD5329	Approved
0.6327	Remote Similarity	NPD7640	Approved
0.6327	Remote Similarity	NPD7639	Approved
0.6322	Remote Similarity	NPD6928	Phase 2
0.6322	Remote Similarity	NPD7525	Registered
0.6316	Remote Similarity	NPD7748	Approved
0.6311	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6373	Approved
0.6304	Remote Similarity	NPD6903	Approved
0.6289	Remote Similarity	NPD4755	Approved
0.6282	Remote Similarity	NPD7909	Approved
0.6279	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6411	Approved
0.6277	Remote Similarity	NPD5284	Approved
0.6277	Remote Similarity	NPD5281	Approved
0.6277	Remote Similarity	NPD7637	Suspended
0.6275	Remote Similarity	NPD5701	Approved
0.6275	Remote Similarity	NPD5697	Approved
0.6264	Remote Similarity	NPD6098	Approved
0.6264	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD4692	Approved
0.625	Remote Similarity	NPD4139	Approved
0.6237	Remote Similarity	NPD6904	Approved
0.6237	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6673	Approved
0.6237	Remote Similarity	NPD6080	Approved
0.6222	Remote Similarity	NPD3668	Phase 3
0.6222	Remote Similarity	NPD4197	Approved
0.6211	Remote Similarity	NPD4202	Approved
0.6204	Remote Similarity	NPD7115	Discovery
0.62	Remote Similarity	NPD7632	Discontinued
0.6197	Remote Similarity	NPD9638	Phase 2
0.619	Remote Similarity	NPD6650	Approved
0.619	Remote Similarity	NPD6847	Approved
0.619	Remote Similarity	NPD8130	Phase 1
0.619	Remote Similarity	NPD6869	Approved
0.619	Remote Similarity	NPD6617	Approved
0.619	Remote Similarity	NPD6649	Approved
0.6186	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5222	Approved
0.6186	Remote Similarity	NPD4697	Phase 3
0.6186	Remote Similarity	NPD5221	Approved
0.6176	Remote Similarity	NPD634	Phase 3
0.6162	Remote Similarity	NPD5286	Approved
0.6162	Remote Similarity	NPD5285	Approved
0.6162	Remote Similarity	NPD4700	Approved
0.6162	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6132	Remote Similarity	NPD6882	Approved
0.6132	Remote Similarity	NPD8297	Approved
0.6125	Remote Similarity	NPD375	Phase 2
0.6122	Remote Similarity	NPD7902	Approved
0.6122	Remote Similarity	NPD5173	Approved
0.6118	Remote Similarity	NPD6942	Approved
0.6118	Remote Similarity	NPD7339	Approved
0.6111	Remote Similarity	NPD6940	Discontinued
0.6111	Remote Similarity	NPD3186	Phase 1
0.61	Remote Similarity	NPD1700	Approved
0.6098	Remote Similarity	NPD3725	Approved
0.6098	Remote Similarity	NPD3726	Approved
0.6087	Remote Similarity	NPD4690	Approved
0.6087	Remote Similarity	NPD4688	Approved
0.6087	Remote Similarity	NPD4689	Approved
0.6087	Remote Similarity	NPD4693	Phase 3
0.6087	Remote Similarity	NPD4138	Approved
0.6087	Remote Similarity	NPD5205	Approved
0.6082	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD8133	Approved
0.6075	Remote Similarity	NPD8298	Phase 2
0.6067	Remote Similarity	NPD5369	Approved
0.6064	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6101	Approved
0.6058	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6011	Approved
0.604	Remote Similarity	NPD5211	Phase 2
0.604	Remote Similarity	NPD5224	Approved
0.604	Remote Similarity	NPD5225	Approved
0.604	Remote Similarity	NPD5226	Approved
0.604	Remote Similarity	NPD4633	Approved
0.6038	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6920	Discontinued
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD2266	Phase 2
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5174	Approved
0.598	Remote Similarity	NPD5175	Approved
0.5976	Remote Similarity	NPD229	Approved
0.5962	Remote Similarity	NPD6412	Phase 2
0.5957	Remote Similarity	NPD5208	Approved
0.5957	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5368	Approved
0.5943	Remote Similarity	NPD4634	Approved
0.5941	Remote Similarity	NPD5223	Approved
0.5938	Remote Similarity	NPD6050	Approved
0.5938	Remote Similarity	NPD5693	Phase 1
0.5922	Remote Similarity	NPD5141	Approved
0.5914	Remote Similarity	NPD4694	Approved
0.5914	Remote Similarity	NPD5690	Phase 2
0.5914	Remote Similarity	NPD5280	Approved
0.5893	Remote Similarity	NPD6319	Approved
0.5876	Remote Similarity	NPD8171	Discontinued
0.5865	Remote Similarity	NPD4767	Approved
0.5865	Remote Similarity	NPD4768	Approved
0.5862	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7614	Phase 1
0.5842	Remote Similarity	NPD6404	Discontinued
0.5833	Remote Similarity	NPD5785	Approved
0.5833	Remote Similarity	NPD5692	Phase 3
0.5826	Remote Similarity	NPD7492	Approved
0.5825	Remote Similarity	NPD4754	Approved
0.5824	Remote Similarity	NPD6435	Approved
0.5818	Remote Similarity	NPD6868	Approved
0.5818	Remote Similarity	NPD6274	Approved
0.5816	Remote Similarity	NPD7900	Approved
0.5816	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6926	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