NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.13
Volume:	249.412
LogP:	1.138
LogD:	0.728
LogS:	-2.143
# Rotatable Bonds:	1
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.653
Synthetic Accessibility Score:	4.201
Fsp3:	0.643
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:	-4.511
MDCK Permeability:	4.46397862106096e-05
Pgp-inhibitor:	0.414
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.479
Plasma Protein Binding (PPB):	66.76455688476562%
Volume Distribution (VD):	0.434
Pgp-substrate:	44.97761917114258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.145
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	7.95
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.572
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.386
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.308
Skin Sensitization:	0.614
Carcinogencity:	0.958
Eye Corrosion:	0.259
Eye Irritation:	0.302
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC203403

Natural Product ID:	NPC203403
*Common Name:**	1Beta-Hydroxy-8,11-Dioxoeremophi-12-Nor-6,9-Diene
IUPAC Name:	(4aS,5S,8R)-3-acetyl-8-hydroxy-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one
Synonyms:
Standard InCHIKey:	DVTGOUULAGTLMM-REAQECSSSA-N
Standard InCHI:	InChI=1S/C14H18O3/c1-8-4-5-12(16)11-6-13(17)10(9(2)15)7-14(8,11)3/h6-8,12,16H,4-5H2,1-3H3/t8-,12+,14+/m0/s1
SMILES:	C[C@H]1CC[C@H](C2=CC(=O)C(=C[C@]12C)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3298263
PubChem CID:	90683034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane 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
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24913558]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26428	Ligularia sagitta	Species	Asteraceae	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	250.0	ug.mL-1	PMID[533202]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	250.0	ug.mL-1	PMID[533202]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[533202]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	31.25	ug.mL-1	PMID[533202]
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	MIC	>	250.0	ug.mL-1	PMID[533202]

☑ 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 NPC203403 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	156
0.1-0.2	1074
0.2-0.3	5270
0.3-0.4	14418
0.4-0.5	10599
0.5-0.6	6651
0.6-0.7	3642
0.7-0.8	817
0.8-0.85	55
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC471514
0.8947	High Similarity	NPC308038
0.8846	High Similarity	NPC93590
0.88	High Similarity	NPC250621
0.8684	High Similarity	NPC74995
0.859	High Similarity	NPC172013
0.8571	High Similarity	NPC62336
0.8553	High Similarity	NPC263582
0.8481	Intermediate Similarity	NPC6663
0.8462	Intermediate Similarity	NPC281138
0.8462	Intermediate Similarity	NPC170394
0.8442	Intermediate Similarity	NPC197659
0.8415	Intermediate Similarity	NPC472985
0.8415	Intermediate Similarity	NPC472974
0.8415	Intermediate Similarity	NPC472986
0.8356	Intermediate Similarity	NPC117804
0.8356	Intermediate Similarity	NPC96484
0.8354	Intermediate Similarity	NPC104120
0.8354	Intermediate Similarity	NPC148685
0.8354	Intermediate Similarity	NPC157895
0.8333	Intermediate Similarity	NPC472983
0.8333	Intermediate Similarity	NPC472973
0.8333	Intermediate Similarity	NPC475994
0.8272	Intermediate Similarity	NPC105173
0.8228	Intermediate Similarity	NPC152061
0.8228	Intermediate Similarity	NPC19900
0.8205	Intermediate Similarity	NPC149550
0.8205	Intermediate Similarity	NPC266193
0.8205	Intermediate Similarity	NPC257666
0.8205	Intermediate Similarity	NPC85105
0.8205	Intermediate Similarity	NPC470428
0.8193	Intermediate Similarity	NPC194417
0.8171	Intermediate Similarity	NPC476412
0.8158	Intermediate Similarity	NPC186042
0.814	Intermediate Similarity	NPC472978
0.8125	Intermediate Similarity	NPC281880
0.8118	Intermediate Similarity	NPC309603
0.8118	Intermediate Similarity	NPC473999
0.8118	Intermediate Similarity	NPC473100
0.8101	Intermediate Similarity	NPC476949
0.8101	Intermediate Similarity	NPC178852
0.8077	Intermediate Similarity	NPC472305
0.8077	Intermediate Similarity	NPC470525
0.8072	Intermediate Similarity	NPC109528
0.8072	Intermediate Similarity	NPC476426
0.8068	Intermediate Similarity	NPC476245
0.8049	Intermediate Similarity	NPC297398
0.8049	Intermediate Similarity	NPC169941
0.8049	Intermediate Similarity	NPC251475
0.8049	Intermediate Similarity	NPC79945
0.8049	Intermediate Similarity	NPC64600
0.8046	Intermediate Similarity	NPC109305
0.8026	Intermediate Similarity	NPC95863
0.8025	Intermediate Similarity	NPC159148
0.8023	Intermediate Similarity	NPC134321
0.8023	Intermediate Similarity	NPC473099
0.8	Intermediate Similarity	NPC104560
0.8	Intermediate Similarity	NPC470429
0.7975	Intermediate Similarity	NPC97377
0.7973	Intermediate Similarity	NPC96962
0.7955	Intermediate Similarity	NPC472977
0.7955	Intermediate Similarity	NPC472976
0.7952	Intermediate Similarity	NPC472265
0.7952	Intermediate Similarity	NPC40687
0.7949	Intermediate Similarity	NPC114236
0.7931	Intermediate Similarity	NPC475806
0.7931	Intermediate Similarity	NPC473998
0.7931	Intermediate Similarity	NPC472975
0.7931	Intermediate Similarity	NPC116726
0.7927	Intermediate Similarity	NPC38796
0.7927	Intermediate Similarity	NPC92226
0.7927	Intermediate Similarity	NPC158411
0.7922	Intermediate Similarity	NPC247586
0.7907	Intermediate Similarity	NPC314727
0.7907	Intermediate Similarity	NPC50488
0.7907	Intermediate Similarity	NPC262858
0.7907	Intermediate Similarity	NPC474396
0.7907	Intermediate Similarity	NPC472240
0.7901	Intermediate Similarity	NPC472301
0.7901	Intermediate Similarity	NPC271104
0.7901	Intermediate Similarity	NPC45495
0.7895	Intermediate Similarity	NPC34834
0.7867	Intermediate Similarity	NPC471238
0.7857	Intermediate Similarity	NPC15807
0.7857	Intermediate Similarity	NPC470574
0.7848	Intermediate Similarity	NPC253190
0.7848	Intermediate Similarity	NPC1973
0.7848	Intermediate Similarity	NPC167873
0.7841	Intermediate Similarity	NPC69454
0.7831	Intermediate Similarity	NPC57370
0.7821	Intermediate Similarity	NPC215050
0.7821	Intermediate Similarity	NPC306727
0.7816	Intermediate Similarity	NPC128672
0.7816	Intermediate Similarity	NPC230332
0.7816	Intermediate Similarity	NPC48010
0.7792	Intermediate Similarity	NPC23954
0.7792	Intermediate Similarity	NPC477792
0.7792	Intermediate Similarity	NPC474884
0.7791	Intermediate Similarity	NPC158778
0.7778	Intermediate Similarity	NPC117133
0.7778	Intermediate Similarity	NPC7232
0.7778	Intermediate Similarity	NPC202833
0.7765	Intermediate Similarity	NPC198761
0.7765	Intermediate Similarity	NPC473226
0.7765	Intermediate Similarity	NPC179591
0.7763	Intermediate Similarity	NPC474248
0.7753	Intermediate Similarity	NPC299100
0.7753	Intermediate Similarity	NPC8993
0.7753	Intermediate Similarity	NPC196227
0.775	Intermediate Similarity	NPC476007
0.775	Intermediate Similarity	NPC34110
0.7738	Intermediate Similarity	NPC33913
0.7738	Intermediate Similarity	NPC472326
0.7738	Intermediate Similarity	NPC302360
0.7738	Intermediate Similarity	NPC470812
0.7733	Intermediate Similarity	NPC106613
0.7727	Intermediate Similarity	NPC233116
0.7727	Intermediate Similarity	NPC212948
0.7727	Intermediate Similarity	NPC63748
0.7722	Intermediate Similarity	NPC474885
0.7711	Intermediate Similarity	NPC256112
0.7711	Intermediate Similarity	NPC279186
0.7711	Intermediate Similarity	NPC2524
0.7711	Intermediate Similarity	NPC48362
0.7711	Intermediate Similarity	NPC103486
0.7701	Intermediate Similarity	NPC123912
0.7701	Intermediate Similarity	NPC472971
0.7701	Intermediate Similarity	NPC472970
0.7701	Intermediate Similarity	NPC146554
0.7701	Intermediate Similarity	NPC119416
0.7692	Intermediate Similarity	NPC323437
0.7692	Intermediate Similarity	NPC220939
0.7692	Intermediate Similarity	NPC265485
0.7692	Intermediate Similarity	NPC287668
0.7692	Intermediate Similarity	NPC471916
0.7692	Intermediate Similarity	NPC253826
0.7692	Intermediate Similarity	NPC201562
0.7692	Intermediate Similarity	NPC29542
0.7683	Intermediate Similarity	NPC476809
0.7683	Intermediate Similarity	NPC2482
0.7674	Intermediate Similarity	NPC109900
0.7674	Intermediate Similarity	NPC287079
0.7667	Intermediate Similarity	NPC259286
0.7667	Intermediate Similarity	NPC180950
0.7667	Intermediate Similarity	NPC271195
0.7662	Intermediate Similarity	NPC92801
0.7662	Intermediate Similarity	NPC286154
0.7654	Intermediate Similarity	NPC476314
0.7654	Intermediate Similarity	NPC297996
0.7654	Intermediate Similarity	NPC80088
0.7654	Intermediate Similarity	NPC253561
0.7654	Intermediate Similarity	NPC275494
0.7654	Intermediate Similarity	NPC471409
0.7647	Intermediate Similarity	NPC179006
0.7647	Intermediate Similarity	NPC474853
0.7647	Intermediate Similarity	NPC474083
0.7647	Intermediate Similarity	NPC52628
0.7647	Intermediate Similarity	NPC471224
0.7647	Intermediate Similarity	NPC274724
0.764	Intermediate Similarity	NPC214697
0.764	Intermediate Similarity	NPC474736
0.7625	Intermediate Similarity	NPC265588
0.7625	Intermediate Similarity	NPC7629
0.7625	Intermediate Similarity	NPC151622
0.7625	Intermediate Similarity	NPC76966
0.7625	Intermediate Similarity	NPC186554
0.7614	Intermediate Similarity	NPC38952
0.7614	Intermediate Similarity	NPC85173
0.7614	Intermediate Similarity	NPC182136
0.7614	Intermediate Similarity	NPC19771
0.7614	Intermediate Similarity	NPC191684
0.7609	Intermediate Similarity	NPC103051
0.7609	Intermediate Similarity	NPC478056
0.76	Intermediate Similarity	NPC202017
0.7595	Intermediate Similarity	NPC78527
0.7595	Intermediate Similarity	NPC470299
0.7595	Intermediate Similarity	NPC201048
0.7595	Intermediate Similarity	NPC476366
0.759	Intermediate Similarity	NPC14151
0.759	Intermediate Similarity	NPC226068
0.759	Intermediate Similarity	NPC6434
0.759	Intermediate Similarity	NPC170303
0.759	Intermediate Similarity	NPC121984
0.759	Intermediate Similarity	NPC116797
0.759	Intermediate Similarity	NPC136150
0.759	Intermediate Similarity	NPC473420
0.759	Intermediate Similarity	NPC470298
0.7586	Intermediate Similarity	NPC7280
0.7586	Intermediate Similarity	NPC229612
0.7586	Intermediate Similarity	NPC471722
0.7586	Intermediate Similarity	NPC473229
0.7586	Intermediate Similarity	NPC206060
0.7586	Intermediate Similarity	NPC48107
0.7586	Intermediate Similarity	NPC471793
0.7586	Intermediate Similarity	NPC472802
0.7586	Intermediate Similarity	NPC471791
0.7586	Intermediate Similarity	NPC328539
0.7582	Intermediate Similarity	NPC301534
0.7582	Intermediate Similarity	NPC250757
0.7582	Intermediate Similarity	NPC249954

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 NPC203403 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1470
0.2-0.3	4099
0.3-0.4	2481
0.4-0.5	555
0.5-0.6	208
0.6-0.7	178
0.7-0.8	11
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
0.7765	Intermediate Similarity	NPD3618	Phase 1
0.7529	Intermediate Similarity	NPD3666	Approved
0.7529	Intermediate Similarity	NPD3133	Approved
0.7529	Intermediate Similarity	NPD3665	Phase 1
0.7528	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD8264	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7442	Intermediate Similarity	NPD1696	Phase 3
0.7356	Intermediate Similarity	NPD5279	Phase 3
0.7333	Intermediate Similarity	NPD7515	Phase 2
0.7326	Intermediate Similarity	NPD4786	Approved
0.7262	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4695	Discontinued
0.7253	Intermediate Similarity	NPD4202	Approved
0.7234	Intermediate Similarity	NPD4225	Approved
0.7204	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5221	Approved
0.7204	Intermediate Similarity	NPD5222	Approved
0.7188	Intermediate Similarity	NPD5211	Phase 2
0.7159	Intermediate Similarity	NPD4519	Discontinued
0.7159	Intermediate Similarity	NPD4623	Approved
0.7128	Intermediate Similarity	NPD5173	Approved
0.7067	Intermediate Similarity	NPD368	Approved
0.7045	Intermediate Similarity	NPD1694	Approved
0.7041	Intermediate Similarity	NPD5141	Approved
0.7021	Intermediate Similarity	NPD4697	Phase 3
0.6989	Remote Similarity	NPD7748	Approved
0.6988	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7639	Approved
0.6979	Remote Similarity	NPD5285	Approved
0.6979	Remote Similarity	NPD5286	Approved
0.6979	Remote Similarity	NPD4696	Approved
0.6979	Remote Similarity	NPD7640	Approved
0.6947	Remote Similarity	NPD4755	Approved
0.6941	Remote Similarity	NPD4195	Approved
0.6941	Remote Similarity	NPD7645	Phase 2
0.6923	Remote Similarity	NPD4753	Phase 2
0.6907	Remote Similarity	NPD5223	Approved
0.6897	Remote Similarity	NPD4221	Approved
0.6897	Remote Similarity	NPD4223	Phase 3
0.6875	Remote Similarity	NPD7638	Approved
0.6867	Remote Similarity	NPD7339	Approved
0.6867	Remote Similarity	NPD6942	Approved
0.6837	Remote Similarity	NPD5224	Approved
0.6837	Remote Similarity	NPD5226	Approved
0.6837	Remote Similarity	NPD4633	Approved
0.6837	Remote Similarity	NPD5225	Approved
0.6824	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4700	Approved
0.6778	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5690	Phase 2
0.6771	Remote Similarity	NPD7902	Approved
0.6768	Remote Similarity	NPD5174	Approved
0.6768	Remote Similarity	NPD5175	Approved
0.6747	Remote Similarity	NPD6926	Approved
0.6747	Remote Similarity	NPD6924	Approved
0.6744	Remote Similarity	NPD6929	Approved
0.6742	Remote Similarity	NPD3668	Phase 3
0.6742	Remote Similarity	NPD4197	Approved
0.6737	Remote Similarity	NPD4629	Approved
0.6737	Remote Similarity	NPD5210	Approved
0.6712	Remote Similarity	NPD342	Phase 1
0.6707	Remote Similarity	NPD7152	Approved
0.6707	Remote Similarity	NPD7151	Approved
0.6707	Remote Similarity	NPD7150	Approved
0.6706	Remote Similarity	NPD5776	Phase 2
0.6706	Remote Similarity	NPD6925	Approved
0.6705	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6628	Remote Similarity	NPD7145	Approved
0.6628	Remote Similarity	NPD3617	Approved
0.66	Remote Similarity	NPD4754	Approved
0.6596	Remote Similarity	NPD7637	Suspended
0.6593	Remote Similarity	NPD7334	Approved
0.6593	Remote Similarity	NPD6409	Approved
0.6593	Remote Similarity	NPD5330	Approved
0.6593	Remote Similarity	NPD4688	Approved
0.6593	Remote Similarity	NPD4693	Phase 3
0.6593	Remote Similarity	NPD7146	Approved
0.6593	Remote Similarity	NPD4694	Approved
0.6593	Remote Similarity	NPD5280	Approved
0.6593	Remote Similarity	NPD5205	Approved
0.6593	Remote Similarity	NPD4689	Approved
0.6593	Remote Similarity	NPD4690	Approved
0.6593	Remote Similarity	NPD4138	Approved
0.6593	Remote Similarity	NPD6684	Approved
0.6593	Remote Similarity	NPD7521	Approved
0.6591	Remote Similarity	NPD6902	Approved
0.6588	Remote Similarity	NPD6933	Approved
0.6585	Remote Similarity	NPD7143	Approved
0.6585	Remote Similarity	NPD4691	Approved
0.6585	Remote Similarity	NPD7144	Approved
0.6569	Remote Similarity	NPD5697	Approved
0.6556	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5778	Approved
0.6526	Remote Similarity	NPD6399	Phase 3
0.6526	Remote Similarity	NPD5779	Approved
0.6522	Remote Similarity	NPD3573	Approved
0.6505	Remote Similarity	NPD6881	Approved
0.6505	Remote Similarity	NPD4729	Approved
0.6505	Remote Similarity	NPD4730	Approved
0.6505	Remote Similarity	NPD5128	Approved
0.6505	Remote Similarity	NPD6899	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD5168	Approved
0.65	Remote Similarity	NPD7331	Phase 2
0.6489	Remote Similarity	NPD5785	Approved
0.6484	Remote Similarity	NPD5363	Approved
0.6481	Remote Similarity	NPD7115	Discovery
0.6477	Remote Similarity	NPD7509	Discontinued
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6463	Remote Similarity	NPD4137	Phase 3
0.6458	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7900	Approved
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6903	Approved
0.6444	Remote Similarity	NPD6695	Phase 3
0.6444	Remote Similarity	NPD4788	Approved
0.6444	Remote Similarity	NPD6110	Phase 1
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6421	Remote Similarity	NPD6411	Approved
0.641	Remote Similarity	NPD4194	Approved
0.641	Remote Similarity	NPD4191	Approved
0.641	Remote Similarity	NPD4192	Approved
0.641	Remote Similarity	NPD4193	Approved
0.6408	Remote Similarity	NPD5701	Approved
0.6404	Remote Similarity	NPD6898	Phase 1
0.64	Remote Similarity	NPD4219	Approved
0.6392	Remote Similarity	NPD5695	Phase 3
0.6386	Remote Similarity	NPD4747	Approved
0.6381	Remote Similarity	NPD7102	Approved
0.6381	Remote Similarity	NPD5250	Approved
0.6381	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4634	Approved
0.6381	Remote Similarity	NPD5248	Approved
0.6381	Remote Similarity	NPD5249	Phase 3
0.6381	Remote Similarity	NPD5169	Approved
0.6381	Remote Similarity	NPD5251	Approved
0.6381	Remote Similarity	NPD5247	Approved
0.6381	Remote Similarity	NPD7290	Approved
0.6381	Remote Similarity	NPD6883	Approved
0.6381	Remote Similarity	NPD5135	Approved
0.6375	Remote Similarity	NPD7341	Phase 2
0.6374	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4058	Approved
0.6346	Remote Similarity	NPD7320	Approved
0.6337	Remote Similarity	NPD7632	Discontinued
0.6322	Remote Similarity	NPD6932	Approved
0.6321	Remote Similarity	NPD6649	Approved
0.6321	Remote Similarity	NPD6869	Approved
0.6321	Remote Similarity	NPD6617	Approved
0.6321	Remote Similarity	NPD8130	Phase 1
0.6321	Remote Similarity	NPD5127	Approved
0.6321	Remote Similarity	NPD5215	Approved
0.6321	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD5216	Approved
0.6321	Remote Similarity	NPD6847	Approved
0.6321	Remote Similarity	NPD5217	Approved
0.6316	Remote Similarity	NPD4096	Approved
0.631	Remote Similarity	NPD5276	Approved
0.6304	Remote Similarity	NPD6893	Approved
0.6304	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4748	Discontinued
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6277	Remote Similarity	NPD6672	Approved
0.6277	Remote Similarity	NPD4518	Approved
0.6277	Remote Similarity	NPD5737	Approved
0.6262	Remote Similarity	NPD8297	Approved
0.6262	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5284	Approved
0.6238	Remote Similarity	NPD5344	Discontinued
0.6234	Remote Similarity	NPD287	Approved
0.6224	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6101	Approved
0.6204	Remote Similarity	NPD4632	Approved
0.62	Remote Similarity	NPD5696	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