NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	350.138
LogP:	3.211
LogD:	3.116
LogS:	-3.453
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.794
Synthetic Accessibility Score:	5.512
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.89
MDCK Permeability:	6.439210665121209e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	89.89400482177734%
Volume Distribution (VD):	0.445
Pgp-substrate:	8.705239295959473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.316
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	0.636
Half-life (T1/2):	0.637

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.512
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.397
Skin Sensitization:	0.918
Carcinogencity:	0.444
Eye Corrosion:	0.333
Eye Irritation:	0.452
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC477931

Natural Product ID:	NPC477931
*Common Name:**	(1S,4S,5R,9S,10R,13S,14R)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5,14-dicarboxylic acid
IUPAC Name:	(1S,4S,5R,9S,10R,13S,14R)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5,14-dicarboxylic acid
Synonyms:
Standard InCHIKey:	HITLMPHPGUZLGI-QJNFORGASA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-18-7-3-8-19(2,17(23)24)14(18)6-9-20-10-12(4-5-15(18)20)13(11-20)16(21)22/h12-15H,3-11H2,1-2H3,(H,21,22)(H,23,24)/t12-,13+,14-,15-,18+,19+,20-/m0/s1
SMILES:	C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@@H](C3)[C@@H](C4)C(=O)O)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118708063
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	=	69.6	%	PMID[24997688]
NPT2	Others	Unspecified	IC50	=	5.59	ug/ml	PMID[24997688]
NPT2	Others	Unspecified	Inhibition	=	31.53	%	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 NPC477931 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	283
0.1-0.2	3677
0.2-0.3	17047
0.3-0.4	8041
0.4-0.5	5930
0.5-0.6	4980
0.6-0.7	2204
0.7-0.8	418
0.8-0.85	58
0.85-0.9	38
0.9-0.95	15
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC268736
0.9677	High Similarity	NPC42060
0.9524	High Similarity	NPC478180
0.9524	High Similarity	NPC474221
0.9524	High Similarity	NPC130459
0.9242	High Similarity	NPC469940
0.9231	High Similarity	NPC469941
0.9231	High Similarity	NPC196197
0.9231	High Similarity	NPC64466
0.9231	High Similarity	NPC252032
0.9231	High Similarity	NPC319671
0.9231	High Similarity	NPC476734
0.9091	High Similarity	NPC108131
0.9091	High Similarity	NPC477929
0.9091	High Similarity	NPC477850
0.8971	High Similarity	NPC477930
0.8955	High Similarity	NPC472309
0.8939	High Similarity	NPC474962
0.8841	High Similarity	NPC477934
0.8841	High Similarity	NPC472311
0.8714	High Similarity	NPC477932
0.8714	High Similarity	NPC477933
0.8714	High Similarity	NPC4209
0.8714	High Similarity	NPC246445
0.8696	High Similarity	NPC167702
0.8696	High Similarity	NPC280026
0.8592	High Similarity	NPC317913
0.8592	High Similarity	NPC477919
0.8592	High Similarity	NPC477918
0.8592	High Similarity	NPC180199
0.8592	High Similarity	NPC207010
0.8571	High Similarity	NPC212733
0.8551	High Similarity	NPC244708
0.8551	High Similarity	NPC330659
0.8551	High Similarity	NPC161187
0.8507	High Similarity	NPC470956
0.8507	High Similarity	NPC473225
0.8472	Intermediate Similarity	NPC34046
0.8472	Intermediate Similarity	NPC185465
0.8472	Intermediate Similarity	NPC324700
0.8472	Intermediate Similarity	NPC476732
0.8472	Intermediate Similarity	NPC224802
0.8472	Intermediate Similarity	NPC199965
0.8472	Intermediate Similarity	NPC80089
0.8472	Intermediate Similarity	NPC329117
0.8472	Intermediate Similarity	NPC171426
0.8356	Intermediate Similarity	NPC320144
0.8356	Intermediate Similarity	NPC201276
0.8356	Intermediate Similarity	NPC80891
0.8333	Intermediate Similarity	NPC66105
0.8333	Intermediate Similarity	NPC298168
0.8333	Intermediate Similarity	NPC474404
0.8333	Intermediate Similarity	NPC469791
0.8333	Intermediate Similarity	NPC143133
0.8333	Intermediate Similarity	NPC68828
0.8243	Intermediate Similarity	NPC261616
0.8243	Intermediate Similarity	NPC472853
0.8235	Intermediate Similarity	NPC281203
0.8235	Intermediate Similarity	NPC469724
0.8235	Intermediate Similarity	NPC100917
0.8235	Intermediate Similarity	NPC31187
0.8143	Intermediate Similarity	NPC197701
0.8143	Intermediate Similarity	NPC320549
0.8143	Intermediate Similarity	NPC151018
0.8143	Intermediate Similarity	NPC58057
0.8143	Intermediate Similarity	NPC473267
0.8143	Intermediate Similarity	NPC156277
0.8133	Intermediate Similarity	NPC12933
0.8116	Intermediate Similarity	NPC131892
0.8116	Intermediate Similarity	NPC213178
0.8116	Intermediate Similarity	NPC324607
0.8116	Intermediate Similarity	NPC6120
0.8116	Intermediate Similarity	NPC321732
0.8116	Intermediate Similarity	NPC327728
0.8108	Intermediate Similarity	NPC192744
0.8108	Intermediate Similarity	NPC472310
0.8082	Intermediate Similarity	NPC471035
0.8082	Intermediate Similarity	NPC212661
0.806	Intermediate Similarity	NPC19311
0.806	Intermediate Similarity	NPC230047
0.8028	Intermediate Similarity	NPC232112
0.8028	Intermediate Similarity	NPC310766
0.8026	Intermediate Similarity	NPC289486
0.8026	Intermediate Similarity	NPC477936
0.8026	Intermediate Similarity	NPC30583
0.8026	Intermediate Similarity	NPC121121
0.8026	Intermediate Similarity	NPC477935
0.8026	Intermediate Similarity	NPC61107
0.8	Intermediate Similarity	NPC476731
0.8	Intermediate Similarity	NPC477851
0.7922	Intermediate Similarity	NPC167103
0.7922	Intermediate Similarity	NPC259173
0.7917	Intermediate Similarity	NPC254340
0.7917	Intermediate Similarity	NPC472854
0.7895	Intermediate Similarity	NPC58631
0.7887	Intermediate Similarity	NPC89310
0.7838	Intermediate Similarity	NPC264602
0.7838	Intermediate Similarity	NPC238227
0.7826	Intermediate Similarity	NPC41542
0.7821	Intermediate Similarity	NPC319909
0.7821	Intermediate Similarity	NPC471044
0.7821	Intermediate Similarity	NPC473336
0.7808	Intermediate Similarity	NPC273366
0.7808	Intermediate Similarity	NPC24014
0.7808	Intermediate Similarity	NPC174964
0.7808	Intermediate Similarity	NPC21220
0.7808	Intermediate Similarity	NPC195155
0.7808	Intermediate Similarity	NPC97534
0.7808	Intermediate Similarity	NPC201027
0.7808	Intermediate Similarity	NPC179858
0.7808	Intermediate Similarity	NPC125767
0.7808	Intermediate Similarity	NPC27349
0.7778	Intermediate Similarity	NPC279241
0.7778	Intermediate Similarity	NPC36310
0.7733	Intermediate Similarity	NPC321690
0.7722	Intermediate Similarity	NPC201655
0.7714	Intermediate Similarity	NPC36616
0.7714	Intermediate Similarity	NPC290445
0.7703	Intermediate Similarity	NPC5767
0.7703	Intermediate Similarity	NPC471046
0.7703	Intermediate Similarity	NPC472486
0.7703	Intermediate Similarity	NPC20466
0.7703	Intermediate Similarity	NPC475742
0.7703	Intermediate Similarity	NPC472487
0.7692	Intermediate Similarity	NPC476735
0.7692	Intermediate Similarity	NPC472740
0.7692	Intermediate Similarity	NPC245866
0.7692	Intermediate Similarity	NPC471037
0.7671	Intermediate Similarity	NPC255168
0.7671	Intermediate Similarity	NPC133922
0.7662	Intermediate Similarity	NPC232625
0.7662	Intermediate Similarity	NPC147066
0.7656	Intermediate Similarity	NPC143597
0.7656	Intermediate Similarity	NPC151464
0.7647	Intermediate Similarity	NPC128608
0.7639	Intermediate Similarity	NPC126642
0.7639	Intermediate Similarity	NPC478227
0.7632	Intermediate Similarity	NPC52951
0.7632	Intermediate Similarity	NPC158846
0.7625	Intermediate Similarity	NPC80590
0.7625	Intermediate Similarity	NPC70661
0.7625	Intermediate Similarity	NPC472272
0.7625	Intermediate Similarity	NPC2783
0.7625	Intermediate Similarity	NPC302111
0.7625	Intermediate Similarity	NPC92139
0.7619	Intermediate Similarity	NPC288296
0.7619	Intermediate Similarity	NPC53245
0.7612	Intermediate Similarity	NPC306750
0.7606	Intermediate Similarity	NPC295788
0.76	Intermediate Similarity	NPC112463
0.76	Intermediate Similarity	NPC23884
0.76	Intermediate Similarity	NPC475031
0.76	Intermediate Similarity	NPC221420
0.76	Intermediate Similarity	NPC169389
0.7568	Intermediate Similarity	NPC159789
0.7568	Intermediate Similarity	NPC132064
0.7564	Intermediate Similarity	NPC311642
0.7564	Intermediate Similarity	NPC100366
0.7564	Intermediate Similarity	NPC102156
0.7564	Intermediate Similarity	NPC170985
0.7564	Intermediate Similarity	NPC164289
0.7564	Intermediate Similarity	NPC148740
0.7564	Intermediate Similarity	NPC242771
0.7532	Intermediate Similarity	NPC470609
0.7531	Intermediate Similarity	NPC33768
0.7531	Intermediate Similarity	NPC269360
0.7531	Intermediate Similarity	NPC264005
0.7531	Intermediate Similarity	NPC252714
0.7531	Intermediate Similarity	NPC134197
0.75	Intermediate Similarity	NPC31031
0.75	Intermediate Similarity	NPC472608
0.75	Intermediate Similarity	NPC243594
0.75	Intermediate Similarity	NPC110094
0.75	Intermediate Similarity	NPC26029
0.75	Intermediate Similarity	NPC63020
0.75	Intermediate Similarity	NPC280654
0.75	Intermediate Similarity	NPC260385
0.75	Intermediate Similarity	NPC476810
0.75	Intermediate Similarity	NPC294438
0.75	Intermediate Similarity	NPC184819
0.75	Intermediate Similarity	NPC264317
0.7468	Intermediate Similarity	NPC15821
0.7468	Intermediate Similarity	NPC477852
0.7467	Intermediate Similarity	NPC89294
0.7467	Intermediate Similarity	NPC104806
0.7465	Intermediate Similarity	NPC260319
0.7465	Intermediate Similarity	NPC474954
0.7465	Intermediate Similarity	NPC2568
0.7465	Intermediate Similarity	NPC103647
0.7465	Intermediate Similarity	NPC180777
0.7439	Intermediate Similarity	NPC16377
0.7439	Intermediate Similarity	NPC211162
0.7439	Intermediate Similarity	NPC4309
0.7439	Intermediate Similarity	NPC474719
0.7439	Intermediate Similarity	NPC183374
0.7436	Intermediate Similarity	NPC472229
0.7436	Intermediate Similarity	NPC472230
0.7436	Intermediate Similarity	NPC201912
0.7436	Intermediate Similarity	NPC469745
0.7436	Intermediate Similarity	NPC474870

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 NPC477931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	3644
0.2-0.3	3615
0.3-0.4	911
0.4-0.5	255
0.5-0.6	258
0.6-0.7	102
0.7-0.8	7
0.8-0.85	11
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9365	High Similarity	NPD4224	Phase 2
0.9242	High Similarity	NPD6081	Approved
0.8714	High Similarity	NPD6117	Approved
0.8696	High Similarity	NPD6113	Clinical (unspecified phase)
0.8592	High Similarity	NPD6116	Phase 1
0.8507	High Similarity	NPD5360	Phase 3
0.8507	High Similarity	NPD5361	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD6115	Approved
0.8472	Intermediate Similarity	NPD6118	Approved
0.8472	Intermediate Similarity	NPD6114	Approved
0.8472	Intermediate Similarity	NPD6697	Approved
0.8333	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD3702	Approved
0.8261	Intermediate Similarity	NPD4789	Approved
0.8143	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD4758	Discontinued
0.8116	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3698	Phase 2
0.8	Intermediate Similarity	NPD4244	Approved
0.8	Intermediate Similarity	NPD4245	Approved
0.7887	Intermediate Similarity	NPD5777	Approved
0.7733	Intermediate Similarity	NPD5364	Discontinued
0.7568	Intermediate Similarity	NPD3703	Phase 2
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3671	Phase 1
0.7176	Intermediate Similarity	NPD8035	Phase 2
0.7176	Intermediate Similarity	NPD8034	Phase 2
0.7077	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3617	Approved
0.7037	Intermediate Similarity	NPD4788	Approved
0.6914	Remote Similarity	NPD4221	Approved
0.6914	Remote Similarity	NPD4223	Phase 3
0.6897	Remote Similarity	NPD6399	Phase 3
0.6892	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD634	Phase 3
0.6812	Remote Similarity	NPD3198	Approved
0.679	Remote Similarity	NPD4692	Approved
0.679	Remote Similarity	NPD4139	Approved
0.6782	Remote Similarity	NPD5284	Approved
0.6782	Remote Similarity	NPD5281	Approved
0.6747	Remote Similarity	NPD4786	Approved
0.6747	Remote Similarity	NPD4197	Approved
0.6712	Remote Similarity	NPD375	Phase 2
0.6707	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.663	Remote Similarity	NPD8418	Phase 2
0.6628	Remote Similarity	NPD5737	Approved
0.6628	Remote Similarity	NPD6672	Approved
0.6593	Remote Similarity	NPD6083	Phase 2
0.6593	Remote Similarity	NPD6084	Phase 2
0.6588	Remote Similarity	NPD4690	Approved
0.6588	Remote Similarity	NPD6098	Approved
0.6588	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4689	Approved
0.6588	Remote Similarity	NPD4693	Phase 3
0.6588	Remote Similarity	NPD4688	Approved
0.6588	Remote Similarity	NPD5205	Approved
0.6588	Remote Similarity	NPD4138	Approved
0.6579	Remote Similarity	NPD4787	Phase 1
0.6567	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5695	Phase 3
0.6552	Remote Similarity	NPD4753	Phase 2
0.6552	Remote Similarity	NPD6904	Approved
0.6552	Remote Similarity	NPD6673	Approved
0.6552	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6080	Approved
0.6548	Remote Similarity	NPD3666	Approved
0.6548	Remote Similarity	NPD3133	Approved
0.6548	Remote Similarity	NPD3665	Phase 1
0.6522	Remote Similarity	NPD5696	Approved
0.6515	Remote Similarity	NPD3186	Phase 1
0.6437	Remote Similarity	NPD5208	Approved
0.6437	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5693	Phase 1
0.6404	Remote Similarity	NPD7515	Phase 2
0.6395	Remote Similarity	NPD5280	Approved
0.6395	Remote Similarity	NPD5690	Phase 2
0.6395	Remote Similarity	NPD7521	Approved
0.6395	Remote Similarity	NPD7146	Approved
0.6395	Remote Similarity	NPD6409	Approved
0.6395	Remote Similarity	NPD7334	Approved
0.6395	Remote Similarity	NPD6684	Approved
0.6395	Remote Similarity	NPD5330	Approved
0.6395	Remote Similarity	NPD3618	Phase 1
0.6395	Remote Similarity	NPD4694	Approved
0.6393	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5328	Approved
0.6353	Remote Similarity	NPD3668	Phase 3
0.6316	Remote Similarity	NPD6705	Phase 1
0.6292	Remote Similarity	NPD5692	Phase 3
0.6265	Remote Similarity	NPD4695	Discontinued
0.6264	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD6903	Approved
0.6222	Remote Similarity	NPD6050	Approved
0.6222	Remote Similarity	NPD6079	Approved
0.6222	Remote Similarity	NPD5694	Approved
0.6207	Remote Similarity	NPD5279	Phase 3
0.6196	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5210	Approved
0.6196	Remote Similarity	NPD4629	Approved
0.617	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD2266	Phase 2
0.6154	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD4747	Approved
0.6145	Remote Similarity	NPD4195	Approved
0.6129	Remote Similarity	NPD7614	Phase 1
0.6129	Remote Similarity	NPD5221	Approved
0.6129	Remote Similarity	NPD4697	Phase 3
0.6129	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5222	Approved
0.6122	Remote Similarity	NPD5739	Approved
0.6122	Remote Similarity	NPD7128	Approved
0.6122	Remote Similarity	NPD6402	Approved
0.6122	Remote Similarity	NPD6675	Approved
0.6119	Remote Similarity	NPD9638	Phase 2
0.6118	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5207	Approved
0.6105	Remote Similarity	NPD7639	Approved
0.6105	Remote Similarity	NPD6404	Discontinued
0.6105	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD6001	Approved
0.6076	Remote Similarity	NPD4243	Approved
0.6071	Remote Similarity	NPD6928	Phase 2
0.6071	Remote Similarity	NPD7525	Registered
0.6064	Remote Similarity	NPD4755	Approved
0.6064	Remote Similarity	NPD7902	Approved
0.6064	Remote Similarity	NPD5173	Approved
0.6061	Remote Similarity	NPD5697	Approved
0.6061	Remote Similarity	NPD5701	Approved
0.6027	Remote Similarity	NPD9656	Approved
0.6026	Remote Similarity	NPD3725	Approved
0.6026	Remote Similarity	NPD4137	Phase 3
0.6026	Remote Similarity	NPD3726	Approved
0.6024	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD4802	Phase 2
0.6024	Remote Similarity	NPD4238	Approved
0.6023	Remote Similarity	NPD4519	Discontinued
0.6023	Remote Similarity	NPD4623	Approved
0.6022	Remote Similarity	NPD5654	Approved
0.602	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7909	Approved
0.6	Remote Similarity	NPD345	Approved
0.6	Remote Similarity	NPD343	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD344	Approved
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD7320	Approved
0.5979	Remote Similarity	NPD7632	Discontinued
0.5978	Remote Similarity	NPD5133	Approved
0.5968	Remote Similarity	NPD2270	Approved
0.5949	Remote Similarity	NPD4691	Approved
0.5941	Remote Similarity	NPD6013	Approved
0.5941	Remote Similarity	NPD6373	Approved
0.5941	Remote Similarity	NPD6014	Approved
0.5941	Remote Similarity	NPD6012	Approved
0.5941	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD5285	Approved
0.5938	Remote Similarity	NPD4700	Approved
0.5938	Remote Similarity	NPD5286	Approved
0.5938	Remote Similarity	NPD4696	Approved
0.5934	Remote Similarity	NPD4096	Approved
0.5926	Remote Similarity	NPD4784	Approved
0.5926	Remote Similarity	NPD4785	Approved
0.5902	Remote Similarity	NPD77	Approved
0.5902	Remote Similarity	NPD9448	Phase 2
0.5902	Remote Similarity	NPD9655	Approved
0.5902	Remote Similarity	NPD633	Phase 3
0.5902	Remote Similarity	NPD9450	Approved
0.5897	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5959	Approved
0.5882	Remote Similarity	NPD7102	Approved
0.5882	Remote Similarity	NPD7290	Approved
0.5882	Remote Similarity	NPD6883	Approved
0.5876	Remote Similarity	NPD5223	Approved
0.5865	Remote Similarity	NPD8298	Phase 2
0.5854	Remote Similarity	NPD2257	Approved
0.5854	Remote Similarity	NPD7339	Approved
0.5854	Remote Similarity	NPD6942	Approved
0.5854	Remote Similarity	NPD5275	Approved
0.5854	Remote Similarity	NPD4190	Phase 3
0.5833	Remote Similarity	NPD9438	Approved
0.5833	Remote Similarity	NPD9439	Approved
0.5825	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6650	Approved
0.5825	Remote Similarity	NPD8130	Phase 1
0.5825	Remote Similarity	NPD6617	Approved
0.5825	Remote Similarity	NPD6847	Approved
0.5825	Remote Similarity	NPD6649	Approved
0.5825	Remote Similarity	NPD6869	Approved
0.5816	Remote Similarity	NPD5224	Approved
0.5816	Remote Similarity	NPD5211	Phase 2
0.5816	Remote Similarity	NPD5225	Approved
0.5816	Remote Similarity	NPD5091	Approved
0.5816	Remote Similarity	NPD5226	Approved
0.5816	Remote Similarity	NPD4633	Approved
0.58	Remote Similarity	NPD6920	Discontinued
0.5783	Remote Similarity	NPD3701	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