NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.12
Volume:	208.666
LogP:	1.388
LogD:	0.706
LogS:	-1.394
# Rotatable Bonds:	0
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.551
Synthetic Accessibility Score:	4.281
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.506
MDCK Permeability:	3.1633924663765356e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.932
Plasma Protein Binding (PPB):	58.464935302734375%
Volume Distribution (VD):	0.561
Pgp-substrate:	39.046024322509766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.749
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.609
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.552
CYP3A4-inhibitor:	0.136
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	16.194
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.082
Skin Sensitization:	0.153
Carcinogencity:	0.55
Eye Corrosion:	0.463
Eye Irritation:	0.558
Respiratory Toxicity:	0.773

Download Data

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

Natural Product: NPC19900

Natural Product ID:	NPC19900
*Common Name:**	Desoxo-Narchinol A
IUPAC Name:	(4R,4aS,5R)-4-hydroxy-4a,5-dimethyl-4,5,6,7-tetrahydronaphthalen-1-one
Synonyms:	Desoxo-Narchinol A
Standard InCHIKey:	YWSIMWUTQXMOSD-FXAINCCUSA-N
Standard InCHI:	InChI=1S/C12H16O2/c1-8-4-3-5-9-10(13)6-7-11(14)12(8,9)2/h5-8,11,14H,3-4H2,1-2H3/t8-,11-,12+/m1/s1
SMILES:	O=C1C=C[C@H]([C@@]2(C1=CCC[C@H]2C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1933703
PubChem CID:	56835056
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO30339	Nardostachys chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0040-4039(97)10844-9]
NPO30339	Nardostachys chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18404355]
NPO30339	Nardostachys chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30339	Nardostachys chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6444	Humulus scandens	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1821	Kopsia albiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14809	Talaromyces avellaneus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5497	Stachys chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2741	Ribes sanguineum	Species	Grossulariaceae	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
IC50	11

Activity Type	# Activity
Cell Line	6
CELL-LINE	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	8400.0	nM	PMID[456203]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	3480.0	nM	PMID[456204]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	2050.0	nM	PMID[456204]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	2040.0	nM	PMID[456204]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	3570.0	nM	PMID[456204]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	2110.0	nM	PMID[456204]
NPT23110	CELL-LINE	Microglia	n.a.	IC50	=	4960.0	nM	PMID[456204]
NPT23110	CELL-LINE	Microglia	n.a.	IC50	=	5330.0	nM	PMID[456204]
NPT23110	CELL-LINE	Microglia	n.a.	IC50	=	5840.0	nM	PMID[456204]
NPT23110	CELL-LINE	Microglia	n.a.	IC50	=	3620.0	nM	PMID[456204]
NPT23110	CELL-LINE	Microglia	n.a.	IC50	=	3180.0	nM	PMID[456204]

☑ 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 NPC19900 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	171
0.1-0.2	1082
0.2-0.3	5794
0.3-0.4	14743
0.4-0.5	11018
0.5-0.6	6309
0.6-0.7	3077
0.7-0.8	436
0.8-0.85	49
0.85-0.9	14
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC38796
0.9605	High Similarity	NPC158411
0.9079	High Similarity	NPC475994
0.8919	High Similarity	NPC186042
0.8816	High Similarity	NPC470525
0.8718	High Similarity	NPC308038
0.8667	High Similarity	NPC29542
0.8667	High Similarity	NPC201562
0.8667	High Similarity	NPC323437
0.8659	High Similarity	NPC472974
0.863	High Similarity	NPC117804
0.859	High Similarity	NPC62336
0.8571	High Similarity	NPC263582
0.8553	High Similarity	NPC215050
0.8537	High Similarity	NPC476426
0.8462	Intermediate Similarity	NPC74995
0.8434	Intermediate Similarity	NPC194417
0.8395	Intermediate Similarity	NPC93590
0.8395	Intermediate Similarity	NPC279186
0.8375	Intermediate Similarity	NPC172013
0.8375	Intermediate Similarity	NPC271104
0.8289	Intermediate Similarity	NPC95863
0.8272	Intermediate Similarity	NPC6663
0.8267	Intermediate Similarity	NPC136473
0.825	Intermediate Similarity	NPC152061
0.825	Intermediate Similarity	NPC281138
0.8243	Intermediate Similarity	NPC106613
0.8243	Intermediate Similarity	NPC269985
0.8228	Intermediate Similarity	NPC471061
0.8228	Intermediate Similarity	NPC203403
0.8205	Intermediate Similarity	NPC114236
0.8193	Intermediate Similarity	NPC476412
0.8148	Intermediate Similarity	NPC104120
0.8148	Intermediate Similarity	NPC157895
0.8148	Intermediate Similarity	NPC148685
0.8148	Intermediate Similarity	NPC471514
0.8148	Intermediate Similarity	NPC45495
0.814	Intermediate Similarity	NPC123912
0.8118	Intermediate Similarity	NPC287079
0.8095	Intermediate Similarity	NPC474853
0.8095	Intermediate Similarity	NPC179006
0.8095	Intermediate Similarity	NPC15807
0.8072	Intermediate Similarity	NPC105173
0.8068	Intermediate Similarity	NPC474736
0.8049	Intermediate Similarity	NPC116797
0.8049	Intermediate Similarity	NPC470298
0.8025	Intermediate Similarity	NPC7232
0.8	Intermediate Similarity	NPC118648
0.8	Intermediate Similarity	NPC94666
0.8	Intermediate Similarity	NPC472985
0.8	Intermediate Similarity	NPC475022
0.8	Intermediate Similarity	NPC222613
0.8	Intermediate Similarity	NPC197659
0.8	Intermediate Similarity	NPC472986
0.8	Intermediate Similarity	NPC97377
0.8	Intermediate Similarity	NPC117133
0.7978	Intermediate Similarity	NPC78159
0.7976	Intermediate Similarity	NPC472326
0.7976	Intermediate Similarity	NPC7927
0.7976	Intermediate Similarity	NPC230527
0.7955	Intermediate Similarity	NPC116726
0.7952	Intermediate Similarity	NPC103486
0.7949	Intermediate Similarity	NPC153660
0.7931	Intermediate Similarity	NPC472983
0.7931	Intermediate Similarity	NPC472973
0.7927	Intermediate Similarity	NPC2482
0.7907	Intermediate Similarity	NPC136548
0.7907	Intermediate Similarity	NPC470523
0.7901	Intermediate Similarity	NPC275494
0.7901	Intermediate Similarity	NPC231739
0.7901	Intermediate Similarity	NPC471409
0.7889	Intermediate Similarity	NPC476245
0.7882	Intermediate Similarity	NPC474083
0.7882	Intermediate Similarity	NPC255174
0.7875	Intermediate Similarity	NPC151622
0.7875	Intermediate Similarity	NPC7629
0.7865	Intermediate Similarity	NPC134826
0.7865	Intermediate Similarity	NPC109305
0.7857	Intermediate Similarity	NPC251475
0.7857	Intermediate Similarity	NPC49019
0.7857	Intermediate Similarity	NPC169941
0.7841	Intermediate Similarity	NPC134321
0.7841	Intermediate Similarity	NPC48010
0.7831	Intermediate Similarity	NPC136150
0.7831	Intermediate Similarity	NPC121984
0.7831	Intermediate Similarity	NPC14151
0.7826	Intermediate Similarity	NPC478056
0.7816	Intermediate Similarity	NPC470524
0.7816	Intermediate Similarity	NPC471793
0.7816	Intermediate Similarity	NPC249889
0.7816	Intermediate Similarity	NPC193843
0.7816	Intermediate Similarity	NPC471791
0.7808	Intermediate Similarity	NPC269737
0.7805	Intermediate Similarity	NPC472490
0.7792	Intermediate Similarity	NPC250928
0.7792	Intermediate Similarity	NPC10758
0.7791	Intermediate Similarity	NPC82979
0.7791	Intermediate Similarity	NPC470955
0.7778	Intermediate Similarity	NPC266193
0.7778	Intermediate Similarity	NPC472976
0.7778	Intermediate Similarity	NPC257666
0.7778	Intermediate Similarity	NPC325946
0.7778	Intermediate Similarity	NPC34110
0.7778	Intermediate Similarity	NPC196227
0.7778	Intermediate Similarity	NPC472977
0.7765	Intermediate Similarity	NPC40687
0.7765	Intermediate Similarity	NPC470812
0.7765	Intermediate Similarity	NPC473246
0.7753	Intermediate Similarity	NPC475806
0.7753	Intermediate Similarity	NPC472978
0.775	Intermediate Similarity	NPC476346
0.7738	Intermediate Similarity	NPC212083
0.7727	Intermediate Similarity	NPC310236
0.7727	Intermediate Similarity	NPC473100
0.7727	Intermediate Similarity	NPC309603
0.7727	Intermediate Similarity	NPC214387
0.7727	Intermediate Similarity	NPC119416
0.7727	Intermediate Similarity	NPC473999
0.7722	Intermediate Similarity	NPC275098
0.7722	Intermediate Similarity	NPC247586
0.7717	Intermediate Similarity	NPC470522
0.7717	Intermediate Similarity	NPC135685
0.7711	Intermediate Similarity	NPC472301
0.7711	Intermediate Similarity	NPC472478
0.7711	Intermediate Similarity	NPC108955
0.7703	Intermediate Similarity	NPC288253
0.7701	Intermediate Similarity	NPC312561
0.7701	Intermediate Similarity	NPC58063
0.7701	Intermediate Similarity	NPC220930
0.7701	Intermediate Similarity	NPC272039
0.7692	Intermediate Similarity	NPC472932
0.7692	Intermediate Similarity	NPC259286
0.7684	Intermediate Similarity	NPC111323
0.7683	Intermediate Similarity	NPC297996
0.7683	Intermediate Similarity	NPC178852
0.7683	Intermediate Similarity	NPC189485
0.7683	Intermediate Similarity	NPC478122
0.7683	Intermediate Similarity	NPC74410
0.7674	Intermediate Similarity	NPC32037
0.7674	Intermediate Similarity	NPC274724
0.7674	Intermediate Similarity	NPC70685
0.7674	Intermediate Similarity	NPC52628
0.7674	Intermediate Similarity	NPC471224
0.7667	Intermediate Similarity	NPC472930
0.7667	Intermediate Similarity	NPC69454
0.766	Intermediate Similarity	NPC115862
0.7654	Intermediate Similarity	NPC472305
0.7654	Intermediate Similarity	NPC1254
0.7654	Intermediate Similarity	NPC469646
0.7654	Intermediate Similarity	NPC250621
0.7647	Intermediate Similarity	NPC64600
0.7647	Intermediate Similarity	NPC110150
0.7647	Intermediate Similarity	NPC41539
0.7647	Intermediate Similarity	NPC66764
0.7647	Intermediate Similarity	NPC297398
0.764	Intermediate Similarity	NPC477149
0.764	Intermediate Similarity	NPC69622
0.764	Intermediate Similarity	NPC473099
0.764	Intermediate Similarity	NPC230332
0.764	Intermediate Similarity	NPC128672
0.764	Intermediate Similarity	NPC477147
0.7634	Intermediate Similarity	NPC103051
0.7634	Intermediate Similarity	NPC197386
0.7634	Intermediate Similarity	NPC235464
0.7634	Intermediate Similarity	NPC166745
0.7625	Intermediate Similarity	NPC213223
0.7619	Intermediate Similarity	NPC226068
0.7619	Intermediate Similarity	NPC55869
0.7619	Intermediate Similarity	NPC225515
0.7614	Intermediate Similarity	NPC474854
0.7614	Intermediate Similarity	NPC476796
0.7614	Intermediate Similarity	NPC471722
0.7614	Intermediate Similarity	NPC104560
0.7614	Intermediate Similarity	NPC473229
0.7614	Intermediate Similarity	NPC158778
0.7614	Intermediate Similarity	NPC53454
0.7609	Intermediate Similarity	NPC472941
0.7609	Intermediate Similarity	NPC456
0.7609	Intermediate Similarity	NPC249954
0.7595	Intermediate Similarity	NPC474884
0.7595	Intermediate Similarity	NPC84790
0.7595	Intermediate Similarity	NPC21944
0.759	Intermediate Similarity	NPC476177
0.759	Intermediate Similarity	NPC474113
0.759	Intermediate Similarity	NPC27817
0.7586	Intermediate Similarity	NPC31564
0.7586	Intermediate Similarity	NPC183736
0.7586	Intermediate Similarity	NPC474733
0.7586	Intermediate Similarity	NPC145879
0.7586	Intermediate Similarity	NPC473226
0.7586	Intermediate Similarity	NPC198761
0.7586	Intermediate Similarity	NPC474732
0.7586	Intermediate Similarity	NPC474778
0.7582	Intermediate Similarity	NPC8993
0.7582	Intermediate Similarity	NPC474882
0.7582	Intermediate Similarity	NPC299100
0.7582	Intermediate Similarity	NPC474690
0.7582	Intermediate Similarity	NPC473162
0.7579	Intermediate Similarity	NPC87351
0.7564	Intermediate Similarity	NPC473893

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 NPC19900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1609
0.2-0.3	3961
0.3-0.4	2389
0.4-0.5	653
0.5-0.6	275
0.6-0.7	97
0.7-0.8	8
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
0.7586	Intermediate Similarity	NPD3618	Phase 1
0.7586	Intermediate Similarity	NPD5279	Phase 3
0.7558	Intermediate Similarity	NPD3133	Approved
0.7558	Intermediate Similarity	NPD3665	Phase 1
0.7558	Intermediate Similarity	NPD3666	Approved
0.7531	Intermediate Similarity	NPD8264	Approved
0.7529	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4623	Approved
0.7386	Intermediate Similarity	NPD4519	Discontinued
0.7363	Intermediate Similarity	NPD6079	Approved
0.7356	Intermediate Similarity	NPD4786	Approved
0.7273	Intermediate Similarity	NPD5363	Approved
0.7273	Intermediate Similarity	NPD1696	Phase 3
0.7262	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5785	Approved
0.7191	Intermediate Similarity	NPD5690	Phase 2
0.7143	Intermediate Similarity	NPD5328	Approved
0.7128	Intermediate Similarity	NPD5210	Approved
0.7128	Intermediate Similarity	NPD4629	Approved
0.7093	Intermediate Similarity	NPD4252	Approved
0.7079	Intermediate Similarity	NPD1694	Approved
0.7053	Intermediate Similarity	NPD5221	Approved
0.7053	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5222	Approved
0.7041	Intermediate Similarity	NPD5211	Phase 2
0.6989	Remote Similarity	NPD7515	Phase 2
0.6979	Remote Similarity	NPD5173	Approved
0.6957	Remote Similarity	NPD4753	Phase 2
0.6932	Remote Similarity	NPD4270	Approved
0.6932	Remote Similarity	NPD4269	Approved
0.6932	Remote Similarity	NPD4223	Phase 3
0.6932	Remote Similarity	NPD4221	Approved
0.6915	Remote Similarity	NPD5778	Approved
0.6915	Remote Similarity	NPD4202	Approved
0.6915	Remote Similarity	NPD5779	Approved
0.69	Remote Similarity	NPD5141	Approved
0.6875	Remote Similarity	NPD4697	Phase 3
0.6848	Remote Similarity	NPD4518	Approved
0.6837	Remote Similarity	NPD4696	Approved
0.6837	Remote Similarity	NPD5285	Approved
0.6837	Remote Similarity	NPD5286	Approved
0.6829	Remote Similarity	NPD4691	Approved
0.6813	Remote Similarity	NPD5280	Approved
0.6813	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4694	Approved
0.6809	Remote Similarity	NPD6411	Approved
0.6809	Remote Similarity	NPD5281	Approved
0.6809	Remote Similarity	NPD5284	Approved
0.6786	Remote Similarity	NPD4058	Approved
0.6786	Remote Similarity	NPD4687	Approved
0.6778	Remote Similarity	NPD3668	Phase 3
0.6778	Remote Similarity	NPD4197	Approved
0.6771	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5223	Approved
0.675	Remote Similarity	NPD7331	Phase 2
0.6747	Remote Similarity	NPD5276	Approved
0.6742	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6399	Phase 3
0.6735	Remote Similarity	NPD4225	Approved
0.6707	Remote Similarity	NPD4137	Phase 3
0.6703	Remote Similarity	NPD5329	Approved
0.67	Remote Similarity	NPD5225	Approved
0.67	Remote Similarity	NPD5226	Approved
0.67	Remote Similarity	NPD5224	Approved
0.67	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD368	Approved
0.6634	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD5175	Approved
0.6633	Remote Similarity	NPD7902	Approved
0.6633	Remote Similarity	NPD4755	Approved
0.663	Remote Similarity	NPD6684	Approved
0.663	Remote Similarity	NPD4690	Approved
0.663	Remote Similarity	NPD5786	Approved
0.663	Remote Similarity	NPD4689	Approved
0.663	Remote Similarity	NPD7334	Approved
0.663	Remote Similarity	NPD5205	Approved
0.663	Remote Similarity	NPD7146	Approved
0.663	Remote Similarity	NPD4138	Approved
0.663	Remote Similarity	NPD4688	Approved
0.663	Remote Similarity	NPD7521	Approved
0.663	Remote Similarity	NPD6409	Approved
0.663	Remote Similarity	NPD5330	Approved
0.663	Remote Similarity	NPD4693	Phase 3
0.6627	Remote Similarity	NPD4747	Approved
0.6598	Remote Similarity	NPD5695	Phase 3
0.6596	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6101	Approved
0.6596	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4195	Approved
0.6588	Remote Similarity	NPD5733	Approved
0.6582	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4756	Discovery
0.6526	Remote Similarity	NPD4096	Approved
0.6517	Remote Similarity	NPD7514	Phase 3
0.6517	Remote Similarity	NPD7332	Phase 2
0.65	Remote Similarity	NPD4700	Approved
0.6495	Remote Similarity	NPD5282	Discontinued
0.6494	Remote Similarity	NPD287	Approved
0.6489	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6903	Approved
0.6484	Remote Similarity	NPD4788	Approved
0.6484	Remote Similarity	NPD7154	Phase 3
0.6477	Remote Similarity	NPD4271	Approved
0.6477	Remote Similarity	NPD7145	Approved
0.6477	Remote Similarity	NPD4268	Approved
0.6465	Remote Similarity	NPD6083	Phase 2
0.6465	Remote Similarity	NPD6084	Phase 2
0.6458	Remote Similarity	NPD7637	Suspended
0.6444	Remote Similarity	NPD5369	Approved
0.6444	Remote Similarity	NPD6902	Approved
0.6442	Remote Similarity	NPD5697	Approved
0.6437	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7143	Approved
0.6429	Remote Similarity	NPD7144	Approved
0.642	Remote Similarity	NPD7341	Phase 2
0.6413	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5696	Approved
0.6383	Remote Similarity	NPD3573	Approved
0.6381	Remote Similarity	NPD5168	Approved
0.6381	Remote Similarity	NPD6899	Approved
0.6381	Remote Similarity	NPD4730	Approved
0.6381	Remote Similarity	NPD6011	Approved
0.6381	Remote Similarity	NPD4729	Approved
0.6381	Remote Similarity	NPD6881	Approved
0.6374	Remote Similarity	NPD5209	Approved
0.6364	Remote Similarity	NPD6925	Approved
0.6364	Remote Similarity	NPD5776	Phase 2
0.6355	Remote Similarity	NPD6649	Approved
0.6355	Remote Similarity	NPD6650	Approved
0.6354	Remote Similarity	NPD5207	Approved
0.6353	Remote Similarity	NPD7151	Approved
0.6353	Remote Similarity	NPD7150	Approved
0.6353	Remote Similarity	NPD7152	Approved
0.6341	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3704	Approved
0.6337	Remote Similarity	NPD6404	Discontinued
0.6337	Remote Similarity	NPD7640	Approved
0.6337	Remote Similarity	NPD7639	Approved
0.6333	Remote Similarity	NPD4822	Approved
0.6333	Remote Similarity	NPD4820	Approved
0.6333	Remote Similarity	NPD4819	Approved
0.6333	Remote Similarity	NPD4821	Approved
0.6333	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7900	Approved
0.6322	Remote Similarity	NPD6942	Approved
0.6322	Remote Similarity	NPD7339	Approved
0.6322	Remote Similarity	NPD8039	Approved
0.6321	Remote Similarity	NPD6013	Approved
0.6321	Remote Similarity	NPD6012	Approved
0.6321	Remote Similarity	NPD6014	Approved
0.6316	Remote Similarity	NPD342	Phase 1
0.6316	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD6672	Approved
0.6311	Remote Similarity	NPD4754	Approved
0.631	Remote Similarity	NPD6923	Approved
0.631	Remote Similarity	NPD6922	Approved
0.6304	Remote Similarity	NPD5332	Approved
0.6304	Remote Similarity	NPD5331	Approved
0.6304	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4790	Discontinued
0.6264	Remote Similarity	NPD4692	Approved
0.6264	Remote Similarity	NPD4139	Approved
0.6262	Remote Similarity	NPD5249	Phase 3
0.6262	Remote Similarity	NPD5250	Approved
0.6262	Remote Similarity	NPD4634	Approved
0.6262	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5247	Approved
0.6262	Remote Similarity	NPD5248	Approved
0.6262	Remote Similarity	NPD7102	Approved
0.6262	Remote Similarity	NPD6883	Approved
0.6262	Remote Similarity	NPD7290	Approved
0.6262	Remote Similarity	NPD5251	Approved
0.6262	Remote Similarity	NPD5169	Approved
0.6262	Remote Similarity	NPD5135	Approved
0.625	Remote Similarity	NPD4192	Approved
0.625	Remote Similarity	NPD4194	Approved
0.625	Remote Similarity	NPD4193	Approved
0.625	Remote Similarity	NPD4191	Approved
0.6238	Remote Similarity	NPD7638	Approved
0.6234	Remote Similarity	NPD4219	Approved
0.6226	Remote Similarity	NPD5128	Approved
0.6226	Remote Similarity	NPD6686	Approved
0.6224	Remote Similarity	NPD5133	Approved
0.6222	Remote Similarity	NPD6929	Approved
0.6214	Remote Similarity	NPD5091	Approved
0.6211	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6926	Approved
0.6207	Remote Similarity	NPD6924	Approved
0.6204	Remote Similarity	NPD5216	Approved
0.6204	Remote Similarity	NPD6847	Approved
0.6204	Remote Similarity	NPD5215	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