NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	335.428
LogP:	2.34
LogD:	2.378
LogS:	-3.178
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.816
Synthetic Accessibility Score:	6.299
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:	-5.381
MDCK Permeability:	1.103056547435699e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	94.7023696899414%
Volume Distribution (VD):	0.705
Pgp-substrate:	3.9982597827911377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.334
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.737
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.226
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.292
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	1.314
Half-life (T1/2):	0.726

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.326
Skin Sensitization:	0.9
Carcinogencity:	0.035
Eye Corrosion:	0.941
Eye Irritation:	0.974
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: NPC477850

Natural Product ID:	NPC477850
*Common Name:**	ent-17-Hydroxytrachyloban-18-oic acid
IUPAC Name:	(1R,4R,5R,9R,10R,12S,13R,14R)-13-(hydroxymethyl)-5,9-dimethylpentacyclo[11.2.1.01,10.04,9.012,14]hexadecane-5-carboxylic acid
Synonyms:
Standard InCHIKey:	JNSJEJASVIFCDB-VAHOTRIISA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-17-5-3-6-18(2,16(22)23)14(17)4-7-19-9-13-12(8-15(17)19)20(13,10-19)11-21/h12-15,21H,3-11H2,1-2H3,(H,22,23)/t12-,13+,14+,15-,17-,18+,19+,20+/m0/s1
SMILES:	C[C@]12CCC[C@@]([C@@H]1CC[C@@]34[C@H]2C[C@H]5[C@@H](C3)[C@]5(C4)CO)(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46907040
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
NPO33608	Rhizopus arrhizus	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20481544]

☑ 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	3

Activity Type	# Activity
Cell Line	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2796	Individual Protein	Apoptosis regulator Bcl-X	Homo sapiens	IC50	=	220000	nM	PMID[20481544]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10000	nM	PMID[20481544]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10000	nM	PMID[20481544]

☑ 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 NPC477850 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	338
0.1-0.2	3998
0.2-0.3	17211
0.3-0.4	7642
0.4-0.5	5864
0.5-0.6	5147
0.6-0.7	2016
0.7-0.8	366
0.8-0.85	85
0.85-0.9	24
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC252032
0.9545	High Similarity	NPC476734
0.9545	High Similarity	NPC319671
0.9545	High Similarity	NPC469941
0.9538	High Similarity	NPC474221
0.9538	High Similarity	NPC130459
0.9538	High Similarity	NPC478180
0.9403	High Similarity	NPC477929
0.9254	High Similarity	NPC64466
0.9091	High Similarity	NPC268736
0.9091	High Similarity	NPC477931
0.9091	High Similarity	NPC42060
0.9	High Similarity	NPC280026
0.9	High Similarity	NPC167702
0.9	High Similarity	NPC477930
0.8986	High Similarity	NPC469940
0.8986	High Similarity	NPC473267
0.8971	High Similarity	NPC474962
0.8873	High Similarity	NPC212733
0.8873	High Similarity	NPC472311
0.8784	High Similarity	NPC477851
0.875	High Similarity	NPC477933
0.875	High Similarity	NPC4209
0.875	High Similarity	NPC477932
0.8696	High Similarity	NPC196197
0.8667	High Similarity	NPC12933
0.863	High Similarity	NPC180199
0.863	High Similarity	NPC143133
0.863	High Similarity	NPC298168
0.863	High Similarity	NPC477919
0.863	High Similarity	NPC474404
0.863	High Similarity	NPC317913
0.863	High Similarity	NPC207010
0.8611	High Similarity	NPC273366
0.8611	High Similarity	NPC477934
0.8571	High Similarity	NPC108131
0.8514	High Similarity	NPC34046
0.8514	High Similarity	NPC476732
0.8514	High Similarity	NPC80089
0.8514	High Similarity	NPC224802
0.8514	High Similarity	NPC324700
0.8514	High Similarity	NPC199965
0.8514	High Similarity	NPC185465
0.8514	High Similarity	NPC171426
0.8451	Intermediate Similarity	NPC320549
0.8451	Intermediate Similarity	NPC156277
0.8451	Intermediate Similarity	NPC151018
0.8451	Intermediate Similarity	NPC58057
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
0.84	Intermediate Similarity	NPC320144
0.84	Intermediate Similarity	NPC201276
0.84	Intermediate Similarity	NPC80891
0.8378	Intermediate Similarity	NPC264602
0.8378	Intermediate Similarity	NPC477918
0.8378	Intermediate Similarity	NPC475031
0.8356	Intermediate Similarity	NPC179858
0.8333	Intermediate Similarity	NPC232112
0.8333	Intermediate Similarity	NPC310766
0.831	Intermediate Similarity	NPC476731
0.8286	Intermediate Similarity	NPC474954
0.8267	Intermediate Similarity	NPC329117
0.8219	Intermediate Similarity	NPC472854
0.8219	Intermediate Similarity	NPC254340
0.8205	Intermediate Similarity	NPC259173
0.8194	Intermediate Similarity	NPC89310
0.8194	Intermediate Similarity	NPC472309
0.8182	Intermediate Similarity	NPC58631
0.8158	Intermediate Similarity	NPC472310
0.8158	Intermediate Similarity	NPC52951
0.8125	Intermediate Similarity	NPC70661
0.8125	Intermediate Similarity	NPC302111
0.8108	Intermediate Similarity	NPC24014
0.8108	Intermediate Similarity	NPC21220
0.8108	Intermediate Similarity	NPC195155
0.8108	Intermediate Similarity	NPC174964
0.8108	Intermediate Similarity	NPC125767
0.8108	Intermediate Similarity	NPC27349
0.8108	Intermediate Similarity	NPC97534
0.8101	Intermediate Similarity	NPC319909
0.8082	Intermediate Similarity	NPC330659
0.8082	Intermediate Similarity	NPC244708
0.8082	Intermediate Similarity	NPC161187
0.8077	Intermediate Similarity	NPC30583
0.8077	Intermediate Similarity	NPC289486
0.8077	Intermediate Similarity	NPC61107
0.8077	Intermediate Similarity	NPC477935
0.8077	Intermediate Similarity	NPC121121
0.8052	Intermediate Similarity	NPC472853
0.8052	Intermediate Similarity	NPC261616
0.803	Intermediate Similarity	NPC476735
0.8028	Intermediate Similarity	NPC473225
0.8	Intermediate Similarity	NPC246445
0.8	Intermediate Similarity	NPC5767
0.8	Intermediate Similarity	NPC472487
0.8	Intermediate Similarity	NPC472486
0.8	Intermediate Similarity	NPC475742
0.7975	Intermediate Similarity	NPC245866
0.7973	Intermediate Similarity	NPC133922
0.7949	Intermediate Similarity	NPC469745
0.7927	Intermediate Similarity	NPC146937
0.7895	Intermediate Similarity	NPC66105
0.7895	Intermediate Similarity	NPC23884
0.7895	Intermediate Similarity	NPC221420
0.7895	Intermediate Similarity	NPC68828
0.7875	Intermediate Similarity	NPC471044
0.7875	Intermediate Similarity	NPC476038
0.7875	Intermediate Similarity	NPC194937
0.7875	Intermediate Similarity	NPC473336
0.7867	Intermediate Similarity	NPC159789
0.7848	Intermediate Similarity	NPC477858
0.7848	Intermediate Similarity	NPC477936
0.7848	Intermediate Similarity	NPC170985
0.7838	Intermediate Similarity	NPC474123
0.7831	Intermediate Similarity	NPC24705
0.7831	Intermediate Similarity	NPC56962
0.7792	Intermediate Similarity	NPC321690
0.7778	Intermediate Similarity	NPC294438
0.7778	Intermediate Similarity	NPC469724
0.7778	Intermediate Similarity	NPC103647
0.7778	Intermediate Similarity	NPC264317
0.7778	Intermediate Similarity	NPC31187
0.7778	Intermediate Similarity	NPC283733
0.7778	Intermediate Similarity	NPC260319
0.7778	Intermediate Similarity	NPC201655
0.7778	Intermediate Similarity	NPC180777
0.7778	Intermediate Similarity	NPC281203
0.7778	Intermediate Similarity	NPC470956
0.7778	Intermediate Similarity	NPC2568
0.7778	Intermediate Similarity	NPC100917
0.7763	Intermediate Similarity	NPC20466
0.775	Intermediate Similarity	NPC472744
0.775	Intermediate Similarity	NPC15821
0.7738	Intermediate Similarity	NPC77756
0.7722	Intermediate Similarity	NPC77311
0.7714	Intermediate Similarity	NPC128608
0.7714	Intermediate Similarity	NPC69149
0.7703	Intermediate Similarity	NPC197701
0.7703	Intermediate Similarity	NPC478227
0.7692	Intermediate Similarity	NPC201459
0.7692	Intermediate Similarity	NPC192744
0.7692	Intermediate Similarity	NPC158846
0.7683	Intermediate Similarity	NPC475007
0.7683	Intermediate Similarity	NPC12774
0.7683	Intermediate Similarity	NPC92139
0.7683	Intermediate Similarity	NPC80590
0.7683	Intermediate Similarity	NPC2783
0.7683	Intermediate Similarity	NPC472272
0.7681	Intermediate Similarity	NPC306750
0.7671	Intermediate Similarity	NPC295788
0.7662	Intermediate Similarity	NPC471035
0.7662	Intermediate Similarity	NPC106078
0.7662	Intermediate Similarity	NPC212661
0.7654	Intermediate Similarity	NPC474996
0.7654	Intermediate Similarity	NPC263974
0.7647	Intermediate Similarity	NPC52756
0.7639	Intermediate Similarity	NPC473230
0.7639	Intermediate Similarity	NPC41542
0.7639	Intermediate Similarity	NPC475884
0.7632	Intermediate Similarity	NPC132064
0.7625	Intermediate Similarity	NPC242771
0.7625	Intermediate Similarity	NPC100366
0.7625	Intermediate Similarity	NPC164289
0.7625	Intermediate Similarity	NPC311642
0.7606	Intermediate Similarity	NPC469791
0.7606	Intermediate Similarity	NPC474380
0.7606	Intermediate Similarity	NPC19311
0.7606	Intermediate Similarity	NPC41577
0.7606	Intermediate Similarity	NPC473276
0.7606	Intermediate Similarity	NPC230047
0.76	Intermediate Similarity	NPC279241
0.7595	Intermediate Similarity	NPC470609
0.759	Intermediate Similarity	NPC134197
0.759	Intermediate Similarity	NPC264005
0.759	Intermediate Similarity	NPC33768
0.759	Intermediate Similarity	NPC269360
0.759	Intermediate Similarity	NPC252714
0.7571	Intermediate Similarity	NPC114891
0.7568	Intermediate Similarity	NPC91369
0.7564	Intermediate Similarity	NPC472608
0.7564	Intermediate Similarity	NPC26029
0.7564	Intermediate Similarity	NPC476810
0.7561	Intermediate Similarity	NPC76518
0.7558	Intermediate Similarity	NPC472232
0.7558	Intermediate Similarity	NPC472231
0.7532	Intermediate Similarity	NPC471046
0.7531	Intermediate Similarity	NPC215893
0.7531	Intermediate Similarity	NPC471037
0.75	Intermediate Similarity	NPC183374
0.75	Intermediate Similarity	NPC474719
0.75	Intermediate Similarity	NPC48756
0.75	Intermediate Similarity	NPC474484
0.75	Intermediate Similarity	NPC211162
0.75	Intermediate Similarity	NPC16377
0.75	Intermediate Similarity	NPC280781
0.75	Intermediate Similarity	NPC103754

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 NPC477850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	3751
0.2-0.3	3600
0.3-0.4	828
0.4-0.5	249
0.5-0.6	268
0.6-0.7	48
0.7-0.8	14
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD6113	Clinical (unspecified phase)
0.8806	High Similarity	NPD4224	Phase 2
0.875	High Similarity	NPD6117	Approved
0.8657	High Similarity	NPD3171	Clinical (unspecified phase)
0.863	High Similarity	NPD6116	Phase 1
0.8571	High Similarity	NPD4789	Approved
0.8514	High Similarity	NPD6115	Approved
0.8514	High Similarity	NPD6697	Approved
0.8514	High Similarity	NPD6118	Approved
0.8514	High Similarity	NPD6114	Approved
0.8451	Intermediate Similarity	NPD6081	Approved
0.8451	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD3698	Phase 2
0.8356	Intermediate Similarity	NPD3702	Approved
0.831	Intermediate Similarity	NPD4245	Approved
0.831	Intermediate Similarity	NPD4244	Approved
0.8028	Intermediate Similarity	NPD5360	Phase 3
0.8028	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD5777	Approved
0.7867	Intermediate Similarity	NPD3703	Phase 2
0.7778	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4758	Discontinued
0.7564	Intermediate Similarity	NPD3671	Phase 1
0.7317	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD3198	Approved
0.7125	Intermediate Similarity	NPD5364	Discontinued
0.7045	Intermediate Similarity	NPD8034	Phase 2
0.7045	Intermediate Similarity	NPD8035	Phase 2
0.7024	Intermediate Similarity	NPD4786	Approved
0.6988	Remote Similarity	NPD3667	Approved
0.6974	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4787	Phase 1
0.6824	Remote Similarity	NPD3666	Approved
0.6824	Remote Similarity	NPD3665	Phase 1
0.6824	Remote Similarity	NPD3133	Approved
0.6778	Remote Similarity	NPD6399	Phase 3
0.6707	Remote Similarity	NPD3617	Approved
0.6702	Remote Similarity	NPD8418	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3618	Phase 1
0.6629	Remote Similarity	NPD5328	Approved
0.6629	Remote Similarity	NPD4753	Phase 2
0.6623	Remote Similarity	NPD6705	Phase 1
0.6618	Remote Similarity	NPD3186	Phase 1
0.6588	Remote Similarity	NPD4223	Phase 3
0.6588	Remote Similarity	NPD4221	Approved
0.6517	Remote Similarity	NPD6672	Approved
0.6517	Remote Similarity	NPD5737	Approved
0.6517	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7515	Phase 2
0.6484	Remote Similarity	NPD6079	Approved
0.6477	Remote Similarity	NPD5279	Phase 3
0.6477	Remote Similarity	NPD7146	Approved
0.6477	Remote Similarity	NPD5330	Approved
0.6477	Remote Similarity	NPD6684	Approved
0.6477	Remote Similarity	NPD7334	Approved
0.6477	Remote Similarity	NPD6409	Approved
0.6477	Remote Similarity	NPD7521	Approved
0.6471	Remote Similarity	NPD4139	Approved
0.6471	Remote Similarity	NPD4692	Approved
0.6462	Remote Similarity	NPD634	Phase 3
0.6452	Remote Similarity	NPD5695	Phase 3
0.6437	Remote Similarity	NPD4197	Approved
0.6421	Remote Similarity	NPD5696	Approved
0.6413	Remote Similarity	NPD4202	Approved
0.6364	Remote Similarity	NPD5329	Approved
0.6364	Remote Similarity	NPD375	Phase 2
0.6353	Remote Similarity	NPD6928	Phase 2
0.6333	Remote Similarity	NPD6903	Approved
0.6304	Remote Similarity	NPD5284	Approved
0.6304	Remote Similarity	NPD5281	Approved
0.6292	Remote Similarity	NPD4689	Approved
0.6292	Remote Similarity	NPD4688	Approved
0.6292	Remote Similarity	NPD5205	Approved
0.6292	Remote Similarity	NPD4138	Approved
0.6292	Remote Similarity	NPD6098	Approved
0.6292	Remote Similarity	NPD4690	Approved
0.6292	Remote Similarity	NPD4693	Phase 3
0.6277	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4629	Approved
0.6277	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD3668	Phase 3
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
0.62	Remote Similarity	NPD6402	Approved
0.62	Remote Similarity	NPD7128	Approved
0.62	Remote Similarity	NPD6675	Approved
0.62	Remote Similarity	NPD5739	Approved
0.6186	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7640	Approved
0.617	Remote Similarity	NPD7748	Approved
0.617	Remote Similarity	NPD6001	Approved
0.6163	Remote Similarity	NPD7525	Registered
0.6154	Remote Similarity	NPD5208	Approved
0.6146	Remote Similarity	NPD4755	Approved
0.6146	Remote Similarity	NPD5173	Approved
0.6145	Remote Similarity	NPD7339	Approved
0.6145	Remote Similarity	NPD6942	Approved
0.6139	Remote Similarity	NPD5701	Approved
0.6139	Remote Similarity	NPD5697	Approved
0.6125	Remote Similarity	NPD3725	Approved
0.6125	Remote Similarity	NPD3726	Approved
0.6118	Remote Similarity	NPD5784	Clinical (unspecified phase)
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
0.6104	Remote Similarity	NPD7909	Approved
0.61	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6904	Approved
0.6087	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6673	Approved
0.6087	Remote Similarity	NPD6080	Approved
0.6078	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD6011	Approved
0.6078	Remote Similarity	NPD6899	Approved
0.6078	Remote Similarity	NPD6881	Approved
0.6071	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5133	Approved
0.6061	Remote Similarity	NPD7632	Discontinued
0.6029	Remote Similarity	NPD2266	Phase 2
0.6023	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4700	Approved
0.602	Remote Similarity	NPD5286	Approved
0.602	Remote Similarity	NPD5285	Approved
0.602	Remote Similarity	NPD4696	Approved
0.6019	Remote Similarity	NPD6373	Approved
0.6019	Remote Similarity	NPD6012	Approved
0.6019	Remote Similarity	NPD6372	Approved
0.6019	Remote Similarity	NPD6014	Approved
0.6019	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7902	Approved
0.5962	Remote Similarity	NPD7102	Approved
0.5962	Remote Similarity	NPD7290	Approved
0.5962	Remote Similarity	NPD6883	Approved
0.596	Remote Similarity	NPD5223	Approved
0.5957	Remote Similarity	NPD5693	Phase 1
0.5943	Remote Similarity	NPD8298	Phase 2
0.593	Remote Similarity	NPD4238	Approved
0.593	Remote Similarity	NPD4802	Phase 2
0.5905	Remote Similarity	NPD6650	Approved
0.5905	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6617	Approved
0.5905	Remote Similarity	NPD6847	Approved
0.5905	Remote Similarity	NPD8130	Phase 1
0.5905	Remote Similarity	NPD6649	Approved
0.5905	Remote Similarity	NPD6869	Approved
0.59	Remote Similarity	NPD5211	Phase 2
0.59	Remote Similarity	NPD5226	Approved
0.59	Remote Similarity	NPD4633	Approved
0.59	Remote Similarity	NPD5225	Approved
0.59	Remote Similarity	NPD5224	Approved
0.5882	Remote Similarity	NPD6920	Discontinued
0.5862	Remote Similarity	NPD4195	Approved
0.5859	Remote Similarity	NPD6404	Discontinued
0.5854	Remote Similarity	NPD4747	Approved
0.5851	Remote Similarity	NPD5207	Approved
0.5851	Remote Similarity	NPD5692	Phase 3
0.5849	Remote Similarity	NPD6882	Approved
0.5849	Remote Similarity	NPD8297	Approved
0.5842	Remote Similarity	NPD4754	Approved
0.5842	Remote Similarity	NPD5174	Approved
0.5842	Remote Similarity	NPD5175	Approved
0.5833	Remote Similarity	NPD6940	Discontinued
0.5833	Remote Similarity	NPD6924	Approved
0.5833	Remote Similarity	NPD6926	Approved
0.5816	Remote Similarity	NPD5959	Approved
0.58	Remote Similarity	NPD1700	Approved
0.5795	Remote Similarity	NPD4695	Discontinued
0.5795	Remote Similarity	NPD4748	Discontinued
0.5794	Remote Similarity	NPD4632	Approved
0.5794	Remote Similarity	NPD8133	Approved
0.5789	Remote Similarity	NPD6050	Approved
0.5789	Remote Similarity	NPD5694	Approved
0.5784	Remote Similarity	NPD5141	Approved
0.5783	Remote Similarity	NPD4243	Approved
0.578	Remote Similarity	NPD7115	Discovery
0.5769	Remote Similarity	NPD6415	Discontinued
0.5765	Remote Similarity	NPD2257	Approved
0.5761	Remote Similarity	NPD4519	Discontinued
0.5761	Remote Similarity	NPD4623	Approved
0.5747	Remote Similarity	NPD4777	Suspended
0.5747	Remote Similarity	NPD4776	Phase 2
0.5732	Remote Similarity	NPD4137	Phase 3
0.5728	Remote Similarity	NPD4768	Approved
0.5728	Remote Similarity	NPD6008	Approved
0.5728	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7614	Phase 1
0.5714	Remote Similarity	NPD9656	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