NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.16
Volume:	245.946
LogP:	1.436
LogD:	0.962
LogS:	-1.628
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.719
Synthetic Accessibility Score:	3.615
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.758
MDCK Permeability:	1.6099234926514328e-05
Pgp-inhibitor:	0.183
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.737
Plasma Protein Binding (PPB):	57.64137268066406%
Volume Distribution (VD):	1.016
Pgp-substrate:	38.94780349731445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.424
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.56
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	8.335
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.097
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.143
Skin Sensitization:	0.458
Carcinogencity:	0.037
Eye Corrosion:	0.675
Eye Irritation:	0.853
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC114236

Natural Product ID:	NPC114236
*Common Name:**	(6R,9S)-9,10-Dihydroxy-4-Megastigmen-3-One
IUPAC Name:	(4R)-4-[(3S)-3,4-dihydroxybutyl]-3,5,5-trimethylcyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	RZMRKQQJGBTKOK-JQWIXIFHSA-N
Standard InCHI:	InChI=1S/C13H22O3/c1-9-6-11(16)7-13(2,3)12(9)5-4-10(15)8-14/h6,10,12,14-15H,4-5,7-8H2,1-3H3/t10-,12-/m0/s1
SMILES:	CC1=CC(=O)CC(C)(C)[C@H]1CC[C@@H](CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2331818
PubChem CID:	23583100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
ED50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[543711]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	>	20.0	uM	PMID[543711]

☑ 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 NPC114236 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	172
0.1-0.2	1187
0.2-0.3	5790
0.3-0.4	15804
0.4-0.5	8701
0.5-0.6	6859
0.6-0.7	3528
0.7-0.8	591
0.8-0.85	56
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9041	High Similarity	NPC470525
0.9041	High Similarity	NPC263582
0.8933	High Similarity	NPC308038
0.8919	High Similarity	NPC197659
0.88	High Similarity	NPC475994
0.88	High Similarity	NPC62336
0.8767	High Similarity	NPC470299
0.8701	High Similarity	NPC136150
0.8667	High Similarity	NPC325946
0.8667	High Similarity	NPC74995
0.863	High Similarity	NPC186042
0.859	High Similarity	NPC212083
0.859	High Similarity	NPC93590
0.8571	High Similarity	NPC172013
0.8571	High Similarity	NPC2482
0.8571	High Similarity	NPC45495
0.85	High Similarity	NPC79573
0.8481	Intermediate Similarity	NPC64600
0.8462	Intermediate Similarity	NPC121984
0.8442	Intermediate Similarity	NPC152061
0.8442	Intermediate Similarity	NPC7232
0.8415	Intermediate Similarity	NPC158778
0.8395	Intermediate Similarity	NPC179591
0.8375	Intermediate Similarity	NPC85774
0.8375	Intermediate Similarity	NPC214043
0.8375	Intermediate Similarity	NPC227064
0.8375	Intermediate Similarity	NPC473246
0.8375	Intermediate Similarity	NPC58841
0.8375	Intermediate Similarity	NPC329043
0.8375	Intermediate Similarity	NPC161423
0.8375	Intermediate Similarity	NPC321187
0.8354	Intermediate Similarity	NPC103486
0.8333	Intermediate Similarity	NPC148685
0.8333	Intermediate Similarity	NPC104120
0.8333	Intermediate Similarity	NPC157895
0.8312	Intermediate Similarity	NPC178852
0.8289	Intermediate Similarity	NPC250621
0.8272	Intermediate Similarity	NPC179006
0.8272	Intermediate Similarity	NPC474853
0.8272	Intermediate Similarity	NPC36350
0.8272	Intermediate Similarity	NPC470574
0.8267	Intermediate Similarity	NPC215050
0.825	Intermediate Similarity	NPC169941
0.825	Intermediate Similarity	NPC251475
0.8228	Intermediate Similarity	NPC470298
0.8228	Intermediate Similarity	NPC14151
0.8228	Intermediate Similarity	NPC116797
0.8205	Intermediate Similarity	NPC19900
0.8205	Intermediate Similarity	NPC229204
0.8205	Intermediate Similarity	NPC281138
0.8182	Intermediate Similarity	NPC165711
0.8182	Intermediate Similarity	NPC97377
0.8182	Intermediate Similarity	NPC257666
0.8182	Intermediate Similarity	NPC266193
0.8182	Intermediate Similarity	NPC211279
0.8171	Intermediate Similarity	NPC472974
0.8171	Intermediate Similarity	NPC472986
0.8171	Intermediate Similarity	NPC145879
0.8171	Intermediate Similarity	NPC474733
0.8171	Intermediate Similarity	NPC473168
0.8171	Intermediate Similarity	NPC474732
0.8171	Intermediate Similarity	NPC472985
0.8171	Intermediate Similarity	NPC94666
0.8171	Intermediate Similarity	NPC31564
0.8171	Intermediate Similarity	NPC327115
0.8171	Intermediate Similarity	NPC474778
0.8171	Intermediate Similarity	NPC194417
0.8169	Intermediate Similarity	NPC474304
0.8169	Intermediate Similarity	NPC474329
0.8148	Intermediate Similarity	NPC476412
0.8148	Intermediate Similarity	NPC237712
0.8148	Intermediate Similarity	NPC470812
0.8125	Intermediate Similarity	NPC38796
0.8125	Intermediate Similarity	NPC158411
0.8125	Intermediate Similarity	NPC151519
0.8125	Intermediate Similarity	NPC48362
0.8118	Intermediate Similarity	NPC116726
0.8118	Intermediate Similarity	NPC19114
0.8108	Intermediate Similarity	NPC173321
0.8101	Intermediate Similarity	NPC472478
0.8101	Intermediate Similarity	NPC271104
0.8095	Intermediate Similarity	NPC473100
0.8077	Intermediate Similarity	NPC471409
0.8077	Intermediate Similarity	NPC297996
0.8077	Intermediate Similarity	NPC74410
0.8077	Intermediate Similarity	NPC321180
0.8077	Intermediate Similarity	NPC275494
0.8072	Intermediate Similarity	NPC472324
0.8072	Intermediate Similarity	NPC90652
0.8072	Intermediate Similarity	NPC58063
0.8072	Intermediate Similarity	NPC475740
0.8072	Intermediate Similarity	NPC136548
0.8052	Intermediate Similarity	NPC469646
0.8052	Intermediate Similarity	NPC180886
0.8049	Intermediate Similarity	NPC469948
0.8049	Intermediate Similarity	NPC476426
0.8025	Intermediate Similarity	NPC105173
0.8023	Intermediate Similarity	NPC109305
0.8023	Intermediate Similarity	NPC474736
0.8	Intermediate Similarity	NPC90055
0.8	Intermediate Similarity	NPC3915
0.8	Intermediate Similarity	NPC473420
0.8	Intermediate Similarity	NPC473099
0.7976	Intermediate Similarity	NPC470417
0.7976	Intermediate Similarity	NPC471722
0.7976	Intermediate Similarity	NPC328539
0.7976	Intermediate Similarity	NPC472802
0.7976	Intermediate Similarity	NPC474854
0.7975	Intermediate Similarity	NPC472490
0.7975	Intermediate Similarity	NPC474113
0.7975	Intermediate Similarity	NPC476177
0.7973	Intermediate Similarity	NPC250928
0.7973	Intermediate Similarity	NPC10758
0.7952	Intermediate Similarity	NPC118648
0.7952	Intermediate Similarity	NPC72133
0.7952	Intermediate Similarity	NPC222613
0.7952	Intermediate Similarity	NPC475022
0.7952	Intermediate Similarity	NPC89077
0.7952	Intermediate Similarity	NPC158393
0.7949	Intermediate Similarity	NPC149249
0.7949	Intermediate Similarity	NPC203403
0.7945	Intermediate Similarity	NPC96962
0.7931	Intermediate Similarity	NPC472977
0.7931	Intermediate Similarity	NPC473172
0.7931	Intermediate Similarity	NPC472976
0.7931	Intermediate Similarity	NPC196227
0.7927	Intermediate Similarity	NPC59453
0.7927	Intermediate Similarity	NPC82902
0.7927	Intermediate Similarity	NPC221758
0.7927	Intermediate Similarity	NPC180834
0.7922	Intermediate Similarity	NPC474011
0.7907	Intermediate Similarity	NPC475441
0.7907	Intermediate Similarity	NPC155304
0.7901	Intermediate Similarity	NPC310989
0.7895	Intermediate Similarity	NPC201562
0.7895	Intermediate Similarity	NPC323437
0.7895	Intermediate Similarity	NPC247586
0.7895	Intermediate Similarity	NPC29542
0.7882	Intermediate Similarity	NPC32830
0.7882	Intermediate Similarity	NPC268406
0.7882	Intermediate Similarity	NPC472973
0.7882	Intermediate Similarity	NPC119416
0.7882	Intermediate Similarity	NPC86319
0.7882	Intermediate Similarity	NPC477943
0.7882	Intermediate Similarity	NPC472983
0.7882	Intermediate Similarity	NPC1015
0.7882	Intermediate Similarity	NPC309603
0.7882	Intermediate Similarity	NPC26959
0.7882	Intermediate Similarity	NPC31985
0.7882	Intermediate Similarity	NPC473999
0.7882	Intermediate Similarity	NPC275740
0.7882	Intermediate Similarity	NPC186688
0.7882	Intermediate Similarity	NPC123912
0.7875	Intermediate Similarity	NPC476809
0.7875	Intermediate Similarity	NPC108955
0.7875	Intermediate Similarity	NPC471514
0.7875	Intermediate Similarity	NPC306095
0.7867	Intermediate Similarity	NPC280256
0.7857	Intermediate Similarity	NPC99909
0.7857	Intermediate Similarity	NPC141292
0.7857	Intermediate Similarity	NPC312561
0.7857	Intermediate Similarity	NPC470523
0.7857	Intermediate Similarity	NPC287079
0.7857	Intermediate Similarity	NPC93778
0.7857	Intermediate Similarity	NPC477926
0.7848	Intermediate Similarity	NPC59436
0.7848	Intermediate Similarity	NPC253561
0.7848	Intermediate Similarity	NPC80088
0.7848	Intermediate Similarity	NPC189485
0.7841	Intermediate Similarity	NPC473170
0.7841	Intermediate Similarity	NPC108141
0.7838	Intermediate Similarity	NPC117804
0.7831	Intermediate Similarity	NPC471224
0.7831	Intermediate Similarity	NPC474218
0.7831	Intermediate Similarity	NPC274724
0.7831	Intermediate Similarity	NPC474083
0.7831	Intermediate Similarity	NPC133954
0.7821	Intermediate Similarity	NPC472305
0.7821	Intermediate Similarity	NPC1973
0.7821	Intermediate Similarity	NPC186554
0.7821	Intermediate Similarity	NPC76966
0.7821	Intermediate Similarity	NPC167873
0.7805	Intermediate Similarity	NPC62214
0.7805	Intermediate Similarity	NPC307258
0.7805	Intermediate Similarity	NPC474748
0.7805	Intermediate Similarity	NPC470948
0.7805	Intermediate Similarity	NPC66764
0.7805	Intermediate Similarity	NPC476082
0.7805	Intermediate Similarity	NPC110150
0.7805	Intermediate Similarity	NPC278648
0.7805	Intermediate Similarity	NPC470165
0.7792	Intermediate Similarity	NPC78527
0.7791	Intermediate Similarity	NPC472325
0.7791	Intermediate Similarity	NPC85173
0.7791	Intermediate Similarity	NPC191684
0.7791	Intermediate Similarity	NPC48010
0.7791	Intermediate Similarity	NPC134321
0.7791	Intermediate Similarity	NPC128672
0.7778	Intermediate Similarity	NPC471898
0.7778	Intermediate Similarity	NPC477372

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 NPC114236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1931
0.2-0.3	3848
0.3-0.4	2241
0.4-0.5	550
0.5-0.6	271
0.6-0.7	137
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD3666	Approved
0.8375	Intermediate Similarity	NPD3133	Approved
0.8375	Intermediate Similarity	NPD3665	Phase 1
0.8171	Intermediate Similarity	NPD3618	Phase 1
0.8171	Intermediate Similarity	NPD5279	Phase 3
0.8125	Intermediate Similarity	NPD3667	Approved
0.7927	Intermediate Similarity	NPD4786	Approved
0.7882	Intermediate Similarity	NPD5328	Approved
0.7875	Intermediate Similarity	NPD4695	Discontinued
0.7701	Intermediate Similarity	NPD6079	Approved
0.7701	Intermediate Similarity	NPD7515	Phase 2
0.7683	Intermediate Similarity	NPD4221	Approved
0.7683	Intermediate Similarity	NPD4223	Phase 3
0.7674	Intermediate Similarity	NPD4753	Phase 2
0.7614	Intermediate Similarity	NPD4202	Approved
0.7568	Intermediate Similarity	NPD7331	Phase 2
0.75	Intermediate Similarity	NPD4197	Approved
0.7432	Intermediate Similarity	NPD7341	Phase 2
0.7412	Intermediate Similarity	NPD5329	Approved
0.7407	Intermediate Similarity	NPD3617	Approved
0.7363	Intermediate Similarity	NPD4697	Phase 3
0.7363	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5221	Approved
0.7363	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD7748	Approved
0.7326	Intermediate Similarity	NPD4688	Approved
0.7326	Intermediate Similarity	NPD4694	Approved
0.7326	Intermediate Similarity	NPD6409	Approved
0.7326	Intermediate Similarity	NPD5280	Approved
0.7326	Intermediate Similarity	NPD4690	Approved
0.7326	Intermediate Similarity	NPD6684	Approved
0.7326	Intermediate Similarity	NPD7146	Approved
0.7326	Intermediate Similarity	NPD4693	Phase 3
0.7326	Intermediate Similarity	NPD4689	Approved
0.7326	Intermediate Similarity	NPD4623	Approved
0.7326	Intermediate Similarity	NPD4138	Approved
0.7326	Intermediate Similarity	NPD5205	Approved
0.7326	Intermediate Similarity	NPD4519	Discontinued
0.7326	Intermediate Similarity	NPD7521	Approved
0.7326	Intermediate Similarity	NPD7334	Approved
0.7326	Intermediate Similarity	NPD5690	Phase 2
0.7326	Intermediate Similarity	NPD5330	Approved
0.7294	Intermediate Similarity	NPD3668	Phase 3
0.7283	Intermediate Similarity	NPD5173	Approved
0.7283	Intermediate Similarity	NPD4755	Approved
0.7253	Intermediate Similarity	NPD4629	Approved
0.7253	Intermediate Similarity	NPD5210	Approved
0.7229	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6903	Approved
0.7159	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5286	Approved
0.7128	Intermediate Similarity	NPD4700	Approved
0.7128	Intermediate Similarity	NPD4696	Approved
0.7128	Intermediate Similarity	NPD5285	Approved
0.7126	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6084	Phase 2
0.7097	Intermediate Similarity	NPD7902	Approved
0.7097	Intermediate Similarity	NPD6083	Phase 2
0.7083	Intermediate Similarity	NPD287	Approved
0.7065	Intermediate Similarity	NPD5695	Phase 3
0.7053	Intermediate Similarity	NPD5223	Approved
0.7051	Intermediate Similarity	NPD4137	Phase 3
0.7041	Intermediate Similarity	NPD6412	Phase 2
0.7033	Intermediate Similarity	NPD6399	Phase 3
0.7011	Intermediate Similarity	NPD1696	Phase 3
0.7	Intermediate Similarity	NPD4096	Approved
0.6988	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5224	Approved
0.6979	Remote Similarity	NPD5225	Approved
0.6979	Remote Similarity	NPD5226	Approved
0.6979	Remote Similarity	NPD4633	Approved
0.6979	Remote Similarity	NPD5211	Phase 2
0.6977	Remote Similarity	NPD4788	Approved
0.6966	Remote Similarity	NPD6672	Approved
0.6966	Remote Similarity	NPD5737	Approved
0.6966	Remote Similarity	NPD4518	Approved
0.6962	Remote Similarity	NPD4691	Approved
0.6962	Remote Similarity	NPD4747	Approved
0.6951	Remote Similarity	NPD6933	Approved
0.6951	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5284	Approved
0.6923	Remote Similarity	NPD6411	Approved
0.6923	Remote Similarity	NPD5281	Approved
0.6907	Remote Similarity	NPD5174	Approved
0.6907	Remote Similarity	NPD4754	Approved
0.6907	Remote Similarity	NPD5175	Approved
0.6905	Remote Similarity	NPD4195	Approved
0.6889	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5276	Approved
0.686	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5696	Approved
0.6837	Remote Similarity	NPD5141	Approved
0.6832	Remote Similarity	NPD4634	Approved
0.6829	Remote Similarity	NPD6942	Approved
0.6829	Remote Similarity	NPD7339	Approved
0.6818	Remote Similarity	NPD1694	Approved
0.6774	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7900	Approved
0.6774	Remote Similarity	NPD5282	Discontinued
0.6768	Remote Similarity	NPD6402	Approved
0.6768	Remote Similarity	NPD4767	Approved
0.6768	Remote Similarity	NPD7128	Approved
0.6768	Remote Similarity	NPD5739	Approved
0.6768	Remote Similarity	NPD6675	Approved
0.6768	Remote Similarity	NPD4768	Approved
0.6744	Remote Similarity	NPD4139	Approved
0.6744	Remote Similarity	NPD4692	Approved
0.6711	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4058	Approved
0.6707	Remote Similarity	NPD6926	Approved
0.6707	Remote Similarity	NPD6924	Approved
0.6707	Remote Similarity	NPD4687	Approved
0.6707	Remote Similarity	NPD5733	Approved
0.6706	Remote Similarity	NPD7645	Phase 2
0.6703	Remote Similarity	NPD6101	Approved
0.6703	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5697	Approved
0.67	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD3704	Approved
0.6667	Remote Similarity	NPD5133	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6635	Remote Similarity	NPD4632	Approved
0.6634	Remote Similarity	NPD7320	Approved
0.6634	Remote Similarity	NPD6686	Approved
0.6634	Remote Similarity	NPD6881	Approved
0.6634	Remote Similarity	NPD6011	Approved
0.6634	Remote Similarity	NPD5168	Approved
0.6634	Remote Similarity	NPD4729	Approved
0.6634	Remote Similarity	NPD4730	Approved
0.6634	Remote Similarity	NPD5128	Approved
0.6634	Remote Similarity	NPD6899	Approved
0.663	Remote Similarity	NPD6698	Approved
0.663	Remote Similarity	NPD5785	Approved
0.663	Remote Similarity	NPD46	Approved
0.6629	Remote Similarity	NPD5363	Approved
0.6629	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5368	Approved
0.6627	Remote Similarity	NPD8264	Approved
0.6623	Remote Similarity	NPD3197	Phase 1
0.6593	Remote Similarity	NPD5208	Approved
0.6591	Remote Similarity	NPD6110	Phase 1
0.6579	Remote Similarity	NPD368	Approved
0.6569	Remote Similarity	NPD6372	Approved
0.6569	Remote Similarity	NPD6014	Approved
0.6569	Remote Similarity	NPD6012	Approved
0.6569	Remote Similarity	NPD6013	Approved
0.6569	Remote Similarity	NPD6373	Approved
0.6552	Remote Similarity	NPD5369	Approved
0.6538	Remote Similarity	NPD8297	Approved
0.6538	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6673	Approved
0.6522	Remote Similarity	NPD6904	Approved
0.6522	Remote Similarity	NPD6080	Approved
0.6505	Remote Similarity	NPD5249	Phase 3
0.6505	Remote Similarity	NPD5248	Approved
0.6505	Remote Similarity	NPD5250	Approved
0.6505	Remote Similarity	NPD5169	Approved
0.6505	Remote Similarity	NPD5251	Approved
0.6505	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5135	Approved
0.6505	Remote Similarity	NPD7102	Approved
0.6505	Remote Similarity	NPD7290	Approved
0.6505	Remote Similarity	NPD5247	Approved
0.6505	Remote Similarity	NPD6883	Approved
0.65	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7638	Approved
0.6489	Remote Similarity	NPD5778	Approved
0.6489	Remote Similarity	NPD5779	Approved
0.6477	Remote Similarity	NPD4270	Approved
0.6477	Remote Similarity	NPD4269	Approved
0.6477	Remote Similarity	NPD6435	Approved
0.6458	Remote Similarity	NPD7614	Phase 1
0.6452	Remote Similarity	NPD5207	Approved
0.6452	Remote Similarity	NPD5692	Phase 3
0.6449	Remote Similarity	NPD7115	Discovery
0.6442	Remote Similarity	NPD5216	Approved
0.6442	Remote Similarity	NPD5217	Approved
0.6442	Remote Similarity	NPD6869	Approved
0.6442	Remote Similarity	NPD6847	Approved
0.6442	Remote Similarity	NPD6649	Approved
0.6442	Remote Similarity	NPD5215	Approved
0.6442	Remote Similarity	NPD8130	Phase 1
0.6442	Remote Similarity	NPD5127	Approved
0.6442	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6650	Approved
0.6442	Remote Similarity	NPD6617	Approved
0.6442	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD342	Phase 1
0.6438	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7525	Registered
0.6429	Remote Similarity	NPD8039	Approved
0.6429	Remote Similarity	NPD7639	Approved
0.6429	Remote Similarity	NPD7640	Approved
0.642	Remote Similarity	NPD6923	Approved
0.642	Remote Similarity	NPD6922	Approved
0.642	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3698	Phase 2

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