NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.25
Volume:	361.281
LogP:	4.069
LogD:	3.553
LogS:	-4.252
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.771
Synthetic Accessibility Score:	5.548
Fsp3:	0.952
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.98
MDCK Permeability:	1.6490004782099277e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.328
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.255
Plasma Protein Binding (PPB):	80.6801986694336%
Volume Distribution (VD):	0.5
Pgp-substrate:	9.159016609191895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.681
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.243
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.619
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	12.082
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.134
Human Hepatotoxicity (H-HT):	0.491
Drug-inuced Liver Injury (DILI):	0.506
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.555
Skin Sensitization:	0.903
Carcinogencity:	0.546
Eye Corrosion:	0.038
Eye Irritation:	0.139
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC477929

Natural Product ID:	NPC477929
*Common Name:**	methyl (1S,4S,5R,9S,10R,14S)-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
IUPAC Name:	methyl (1S,4S,5R,9S,10R,14S)-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
Synonyms:
Standard InCHIKey:	HCXQUFPQHLFUCK-WQDJLJQSSA-N
Standard InCHI:	InChI=1S/C21H34O3/c1-19-8-4-9-20(2,18(23)24-3)16(19)7-10-21-11-14(5-6-17(19)21)15(12-21)13-22/h14-17,22H,4-13H2,1-3H3/t14?,15-,16+,17+,19-,20-,21+/m1/s1
SMILES:	C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CCC(C3)[C@H](C4)CO)(C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	163068978
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
GI50	8
IC50	2
Others	2

Activity Type	# Activity
Cell Line	5
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	GI50	>	9020	nM	PMID[23353738]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	>	9020	nM	PMID[23353738]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	>	9020	nM	PMID[23353738]
NPT461	Cell Line	PANC-1	Homo sapiens	GI50	>	9020	nM	PMID[23353738]
NPT111	Cell Line	K562	Homo sapiens	GI50	>	9020	nM	PMID[23353738]
NPT2	Others	Unspecified		GI50	>	9020	nM	PMID[23353738]
NPT2	Others	Unspecified		GI50	=	7230	nM	PMID[23353738]
NPT2	Others	Unspecified		Inhibition	=	90.74	%	PMID[24997688]
NPT2	Others	Unspecified		IC50	=	5.22	ug/ml	PMID[24997688]
NPT2	Others	Unspecified		Inhibition	=	27.7	%	PMID[24997688]
NPT2	Others	Unspecified		IC50	>	10	ug/ml	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 NPC477929 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	284
0.1-0.2	3150
0.2-0.3	15657
0.3-0.4	8730
0.4-0.5	5937
0.5-0.6	5427
0.6-0.7	2763
0.7-0.8	596
0.8-0.85	74
0.85-0.9	51
0.9-0.95	20
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC319671
0.9846	High Similarity	NPC469941
0.9846	High Similarity	NPC252032
0.9846	High Similarity	NPC476734
0.9552	High Similarity	NPC469940
0.9403	High Similarity	NPC477850
0.9385	High Similarity	NPC42060
0.9286	High Similarity	NPC477933
0.9286	High Similarity	NPC477932
0.9275	High Similarity	NPC167702
0.9275	High Similarity	NPC477930
0.9275	High Similarity	NPC280026
0.9254	High Similarity	NPC64466
0.9143	High Similarity	NPC477934
0.9143	High Similarity	NPC212733
0.9091	High Similarity	NPC268736
0.9091	High Similarity	NPC477931
0.9028	High Similarity	NPC476732
0.9028	High Similarity	NPC199965
0.9014	High Similarity	NPC4209
0.8955	High Similarity	NPC130459
0.8955	High Similarity	NPC474221
0.8955	High Similarity	NPC478180
0.8904	High Similarity	NPC80891
0.8904	High Similarity	NPC201276
0.8889	High Similarity	NPC180199
0.8889	High Similarity	NPC477919
0.8889	High Similarity	NPC207010
0.8889	High Similarity	NPC317913
0.8889	High Similarity	NPC298168
0.8889	High Similarity	NPC143133
0.8889	High Similarity	NPC477918
0.8873	High Similarity	NPC472311
0.8841	High Similarity	NPC108131
0.8767	High Similarity	NPC224802
0.8767	High Similarity	NPC171426
0.8767	High Similarity	NPC324700
0.8767	High Similarity	NPC80089
0.8767	High Similarity	NPC34046
0.8767	High Similarity	NPC185465
0.8714	High Similarity	NPC320549
0.8714	High Similarity	NPC151018
0.8714	High Similarity	NPC156277
0.8714	High Similarity	NPC58057
0.8696	High Similarity	NPC196197
0.8696	High Similarity	NPC474962
0.8667	High Similarity	NPC58631
0.8649	High Similarity	NPC320144
0.863	High Similarity	NPC474404
0.8592	High Similarity	NPC232112
0.8592	High Similarity	NPC310766
0.8553	High Similarity	NPC61107
0.8553	High Similarity	NPC477935
0.8553	High Similarity	NPC289486
0.8533	High Similarity	NPC472853
0.8533	High Similarity	NPC261616
0.8514	High Similarity	NPC329117
0.8472	Intermediate Similarity	NPC472854
0.8472	Intermediate Similarity	NPC254340
0.8451	Intermediate Similarity	NPC473267
0.8429	Intermediate Similarity	NPC6120
0.8429	Intermediate Similarity	NPC327728
0.8429	Intermediate Similarity	NPC213178
0.8429	Intermediate Similarity	NPC131892
0.8429	Intermediate Similarity	NPC324607
0.8429	Intermediate Similarity	NPC321732
0.8421	Intermediate Similarity	NPC12933
0.8356	Intermediate Similarity	NPC174964
0.8356	Intermediate Similarity	NPC179858
0.8356	Intermediate Similarity	NPC97534
0.8356	Intermediate Similarity	NPC195155
0.8356	Intermediate Similarity	NPC273366
0.8356	Intermediate Similarity	NPC21220
0.8356	Intermediate Similarity	NPC27349
0.8356	Intermediate Similarity	NPC125767
0.8356	Intermediate Similarity	NPC24014
0.8333	Intermediate Similarity	NPC473336
0.8333	Intermediate Similarity	NPC471044
0.8312	Intermediate Similarity	NPC121121
0.8312	Intermediate Similarity	NPC30583
0.8312	Intermediate Similarity	NPC477936
0.831	Intermediate Similarity	NPC476731
0.8308	Intermediate Similarity	NPC476735
0.8289	Intermediate Similarity	NPC477851
0.8286	Intermediate Similarity	NPC473225
0.8243	Intermediate Similarity	NPC475742
0.8243	Intermediate Similarity	NPC472486
0.8243	Intermediate Similarity	NPC246445
0.8243	Intermediate Similarity	NPC5767
0.8243	Intermediate Similarity	NPC472487
0.8205	Intermediate Similarity	NPC259173
0.8205	Intermediate Similarity	NPC245866
0.8194	Intermediate Similarity	NPC478227
0.8194	Intermediate Similarity	NPC89310
0.8194	Intermediate Similarity	NPC472309
0.8194	Intermediate Similarity	NPC197701
0.8158	Intermediate Similarity	NPC472310
0.8143	Intermediate Similarity	NPC41542
0.8133	Intermediate Similarity	NPC264602
0.8133	Intermediate Similarity	NPC221420
0.8133	Intermediate Similarity	NPC475031
0.8133	Intermediate Similarity	NPC68828
0.8133	Intermediate Similarity	NPC66105
0.8133	Intermediate Similarity	NPC23884
0.8125	Intermediate Similarity	NPC12774
0.8125	Intermediate Similarity	NPC92139
0.8101	Intermediate Similarity	NPC319909
0.8101	Intermediate Similarity	NPC263974
0.8082	Intermediate Similarity	NPC330659
0.8082	Intermediate Similarity	NPC279241
0.8082	Intermediate Similarity	NPC244708
0.8082	Intermediate Similarity	NPC161187
0.8077	Intermediate Similarity	NPC242771
0.8077	Intermediate Similarity	NPC164289
0.8077	Intermediate Similarity	NPC100366
0.8077	Intermediate Similarity	NPC311642
0.8028	Intermediate Similarity	NPC100917
0.8028	Intermediate Similarity	NPC474954
0.8028	Intermediate Similarity	NPC180777
0.8028	Intermediate Similarity	NPC469724
0.8028	Intermediate Similarity	NPC103647
0.8028	Intermediate Similarity	NPC2568
0.8028	Intermediate Similarity	NPC260319
0.8028	Intermediate Similarity	NPC31187
0.8028	Intermediate Similarity	NPC281203
0.8025	Intermediate Similarity	NPC33768
0.8025	Intermediate Similarity	NPC134197
0.8025	Intermediate Similarity	NPC252714
0.8	Intermediate Similarity	NPC201655
0.8	Intermediate Similarity	NPC294438
0.8	Intermediate Similarity	NPC264317
0.8	Intermediate Similarity	NPC471046
0.7975	Intermediate Similarity	NPC471037
0.7973	Intermediate Similarity	NPC133922
0.7949	Intermediate Similarity	NPC48756
0.7949	Intermediate Similarity	NPC280781
0.7941	Intermediate Similarity	NPC306750
0.7922	Intermediate Similarity	NPC201459
0.7922	Intermediate Similarity	NPC245029
0.7922	Intermediate Similarity	NPC52951
0.7922	Intermediate Similarity	NPC31302
0.7922	Intermediate Similarity	NPC192744
0.7917	Intermediate Similarity	NPC295788
0.7917	Intermediate Similarity	NPC178541
0.7901	Intermediate Similarity	NPC472272
0.7901	Intermediate Similarity	NPC80590
0.7901	Intermediate Similarity	NPC2783
0.7901	Intermediate Similarity	NPC70661
0.7901	Intermediate Similarity	NPC302111
0.7895	Intermediate Similarity	NPC171658
0.7867	Intermediate Similarity	NPC159789
0.7857	Intermediate Similarity	NPC230047
0.7857	Intermediate Similarity	NPC19311
0.7848	Intermediate Similarity	NPC148740
0.7848	Intermediate Similarity	NPC170985
0.7848	Intermediate Similarity	NPC102156
0.7838	Intermediate Similarity	NPC474123
0.7826	Intermediate Similarity	NPC114891
0.7821	Intermediate Similarity	NPC470609
0.7808	Intermediate Similarity	NPC91369
0.7805	Intermediate Similarity	NPC269360
0.7805	Intermediate Similarity	NPC264005
0.7792	Intermediate Similarity	NPC471045
0.7792	Intermediate Similarity	NPC26029
0.7792	Intermediate Similarity	NPC31031
0.7792	Intermediate Similarity	NPC243594
0.7792	Intermediate Similarity	NPC63020
0.7792	Intermediate Similarity	NPC472608
0.7778	Intermediate Similarity	NPC283733
0.7778	Intermediate Similarity	NPC470956
0.7763	Intermediate Similarity	NPC476601
0.775	Intermediate Similarity	NPC217559
0.775	Intermediate Similarity	NPC292458
0.775	Intermediate Similarity	NPC268578
0.775	Intermediate Similarity	NPC472744
0.775	Intermediate Similarity	NPC15821
0.7738	Intermediate Similarity	NPC77756
0.7733	Intermediate Similarity	NPC472944
0.7733	Intermediate Similarity	NPC472945
0.7722	Intermediate Similarity	NPC271572
0.7722	Intermediate Similarity	NPC469745
0.7722	Intermediate Similarity	NPC474484
0.7722	Intermediate Similarity	NPC103754
0.7722	Intermediate Similarity	NPC77311
0.7722	Intermediate Similarity	NPC474870
0.7711	Intermediate Similarity	NPC255176
0.7711	Intermediate Similarity	NPC211162
0.7711	Intermediate Similarity	NPC16377
0.7711	Intermediate Similarity	NPC4309
0.7711	Intermediate Similarity	NPC474719
0.7711	Intermediate Similarity	NPC471900
0.7711	Intermediate Similarity	NPC146937
0.7711	Intermediate Similarity	NPC183374
0.7703	Intermediate Similarity	NPC290058
0.7692	Intermediate Similarity	NPC220379
0.7692	Intermediate Similarity	NPC471475
0.7683	Intermediate Similarity	NPC472505
0.7683	Intermediate Similarity	NPC155011
0.7681	Intermediate Similarity	NPC71460
0.7681	Intermediate Similarity	NPC148174

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 NPC477929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	3362
0.2-0.3	3745
0.3-0.4	1018
0.4-0.5	279
0.5-0.6	259
0.6-0.7	117
0.7-0.8	13
0.8-0.85	3
0.85-0.9	16
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9275	High Similarity	NPD6113	Clinical (unspecified phase)
0.9014	High Similarity	NPD6117	Approved
0.8889	High Similarity	NPD6116	Phase 1
0.8841	High Similarity	NPD4789	Approved
0.8806	High Similarity	NPD4224	Phase 2
0.8767	High Similarity	NPD6697	Approved
0.8767	High Similarity	NPD6114	Approved
0.8767	High Similarity	NPD6115	Approved
0.8767	High Similarity	NPD6118	Approved
0.8714	High Similarity	NPD4808	Clinical (unspecified phase)
0.8714	High Similarity	NPD4809	Clinical (unspecified phase)
0.8714	High Similarity	NPD6081	Approved
0.8657	High Similarity	NPD3171	Clinical (unspecified phase)
0.8611	High Similarity	NPD3702	Approved
0.8571	High Similarity	NPD4244	Approved
0.8571	High Similarity	NPD4245	Approved
0.8451	Intermediate Similarity	NPD5777	Approved
0.8429	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD3698	Phase 2
0.8429	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD5360	Phase 3
0.8	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3703	Phase 2
0.7703	Intermediate Similarity	NPD4758	Discontinued
0.7564	Intermediate Similarity	NPD3671	Phase 1
0.7531	Intermediate Similarity	NPD4788	Approved
0.7442	Intermediate Similarity	NPD8034	Phase 2
0.7442	Intermediate Similarity	NPD8035	Phase 2
0.7391	Intermediate Similarity	NPD3198	Approved
0.7342	Intermediate Similarity	NPD5364	Discontinued
0.7229	Intermediate Similarity	NPD4786	Approved
0.72	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6399	Phase 3
0.7105	Intermediate Similarity	NPD4787	Phase 1
0.7033	Intermediate Similarity	NPD6084	Phase 2
0.7033	Intermediate Similarity	NPD6083	Phase 2
0.6988	Remote Similarity	NPD3667	Approved
0.6912	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5737	Approved
0.6897	Remote Similarity	NPD6672	Approved
0.6897	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8418	Phase 2
0.686	Remote Similarity	NPD5330	Approved
0.686	Remote Similarity	NPD7334	Approved
0.686	Remote Similarity	NPD6409	Approved
0.686	Remote Similarity	NPD7521	Approved
0.686	Remote Similarity	NPD7146	Approved
0.686	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD6705	Phase 1
0.6824	Remote Similarity	NPD3666	Approved
0.6824	Remote Similarity	NPD3665	Phase 1
0.6824	Remote Similarity	NPD3133	Approved
0.6818	Remote Similarity	NPD5328	Approved
0.6747	Remote Similarity	NPD6928	Phase 2
0.6707	Remote Similarity	NPD3617	Approved
0.6705	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6079	Approved
0.663	Remote Similarity	NPD5695	Phase 3
0.6629	Remote Similarity	NPD4753	Phase 2
0.6596	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD5696	Approved
0.6588	Remote Similarity	NPD4221	Approved
0.6588	Remote Similarity	NPD4223	Phase 3
0.6552	Remote Similarity	NPD5329	Approved
0.6538	Remote Similarity	NPD3725	Approved
0.6538	Remote Similarity	NPD3726	Approved
0.6531	Remote Similarity	NPD6402	Approved
0.6531	Remote Similarity	NPD6675	Approved
0.6531	Remote Similarity	NPD7128	Approved
0.6531	Remote Similarity	NPD5739	Approved
0.6526	Remote Similarity	NPD7640	Approved
0.6526	Remote Similarity	NPD7639	Approved
0.6522	Remote Similarity	NPD7748	Approved
0.6477	Remote Similarity	NPD5279	Phase 3
0.6471	Remote Similarity	NPD4139	Approved
0.6471	Remote Similarity	NPD4692	Approved
0.6462	Remote Similarity	NPD634	Phase 3
0.6444	Remote Similarity	NPD6904	Approved
0.6444	Remote Similarity	NPD6673	Approved
0.6444	Remote Similarity	NPD6080	Approved
0.6437	Remote Similarity	NPD4197	Approved
0.6429	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4202	Approved
0.64	Remote Similarity	NPD6881	Approved
0.64	Remote Similarity	NPD6899	Approved
0.64	Remote Similarity	NPD7320	Approved
0.6392	Remote Similarity	NPD7632	Discontinued
0.6377	Remote Similarity	NPD3186	Phase 1
0.6364	Remote Similarity	NPD375	Phase 2
0.6353	Remote Similarity	NPD7525	Registered
0.6341	Remote Similarity	NPD7339	Approved
0.6341	Remote Similarity	NPD6942	Approved
0.6337	Remote Similarity	NPD6373	Approved
0.6337	Remote Similarity	NPD6372	Approved
0.6333	Remote Similarity	NPD5208	Approved
0.6316	Remote Similarity	NPD7909	Approved
0.6316	Remote Similarity	NPD7902	Approved
0.631	Remote Similarity	NPD4802	Phase 2
0.631	Remote Similarity	NPD4238	Approved
0.631	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5284	Approved
0.6304	Remote Similarity	NPD5281	Approved
0.63	Remote Similarity	NPD5701	Approved
0.63	Remote Similarity	NPD5697	Approved
0.6292	Remote Similarity	NPD4138	Approved
0.6292	Remote Similarity	NPD4688	Approved
0.6292	Remote Similarity	NPD4689	Approved
0.6292	Remote Similarity	NPD5205	Approved
0.6292	Remote Similarity	NPD4690	Approved
0.6292	Remote Similarity	NPD4693	Phase 3
0.6277	Remote Similarity	NPD4629	Approved
0.6277	Remote Similarity	NPD5210	Approved
0.6277	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7102	Approved
0.6275	Remote Similarity	NPD7290	Approved
0.6275	Remote Similarity	NPD6883	Approved
0.6269	Remote Similarity	NPD2266	Phase 2
0.6264	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3668	Phase 3
0.6238	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD6649	Approved
0.6214	Remote Similarity	NPD6869	Approved
0.6214	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6847	Approved
0.6214	Remote Similarity	NPD6650	Approved
0.6214	Remote Similarity	NPD6617	Approved
0.6214	Remote Similarity	NPD8130	Phase 1
0.6211	Remote Similarity	NPD4697	Phase 3
0.6211	Remote Similarity	NPD5221	Approved
0.6211	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5222	Approved
0.6207	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6920	Discontinued
0.6176	Remote Similarity	NPD6013	Approved
0.6176	Remote Similarity	NPD6014	Approved
0.6176	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD6882	Approved
0.6146	Remote Similarity	NPD5173	Approved
0.6146	Remote Similarity	NPD4755	Approved
0.6132	Remote Similarity	NPD6940	Discontinued
0.6129	Remote Similarity	NPD6050	Approved
0.6129	Remote Similarity	NPD5693	Phase 1
0.6111	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5690	Phase 2
0.6111	Remote Similarity	NPD4694	Approved
0.6111	Remote Similarity	NPD5280	Approved
0.6095	Remote Similarity	NPD8298	Phase 2
0.6095	Remote Similarity	NPD8133	Approved
0.6078	Remote Similarity	NPD6415	Discontinued
0.6071	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD6924	Approved
0.6024	Remote Similarity	NPD6926	Approved
0.6022	Remote Similarity	NPD5207	Approved
0.6022	Remote Similarity	NPD5692	Phase 3
0.602	Remote Similarity	NPD4700	Approved
0.602	Remote Similarity	NPD5286	Approved
0.602	Remote Similarity	NPD6404	Discontinued
0.602	Remote Similarity	NPD5285	Approved
0.602	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6001	Approved
0.5981	Remote Similarity	NPD6868	Approved
0.598	Remote Similarity	NPD6412	Phase 2
0.5976	Remote Similarity	NPD4243	Approved
0.596	Remote Similarity	NPD5223	Approved
0.5957	Remote Similarity	NPD7637	Suspended
0.5957	Remote Similarity	NPD5694	Approved
0.5957	Remote Similarity	NPD6411	Approved
0.5955	Remote Similarity	NPD5362	Discontinued
0.5952	Remote Similarity	NPD2257	Approved
0.5943	Remote Similarity	NPD4632	Approved
0.593	Remote Similarity	NPD4776	Phase 2
0.593	Remote Similarity	NPD4777	Suspended
0.5926	Remote Similarity	NPD7115	Discovery
0.5914	Remote Similarity	NPD6051	Approved
0.5909	Remote Similarity	NPD5369	Approved
0.59	Remote Similarity	NPD5226	Approved
0.59	Remote Similarity	NPD4633	Approved
0.59	Remote Similarity	NPD5225	Approved
0.59	Remote Similarity	NPD5224	Approved
0.59	Remote Similarity	NPD5211	Phase 2
0.5895	Remote Similarity	NPD8171	Discontinued
0.5882	Remote Similarity	NPD6933	Approved
0.5876	Remote Similarity	NPD7614	Phase 1
0.5872	Remote Similarity	NPD6335	Approved
0.5862	Remote Similarity	NPD4195	Approved
0.5862	Remote Similarity	NPD7645	Phase 2
0.5854	Remote Similarity	NPD4747	Approved
0.5846	Remote Similarity	NPD2270	Approved
0.5843	Remote Similarity	NPD6435	Approved
0.5842	Remote Similarity	NPD4754	Approved
0.5842	Remote Similarity	NPD5174	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