NPASS Compound

Structure

NPC474310 OpenBabel07101719142D 28 30 0 0 1 0 0 0 0 0999 V2000 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 9 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 27 1 0 0 0 0 7 10 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 10 1 0 0 0 0 10 14 2 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 17 1 0 0 0 0 16 24 2 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.15
Volume:	389.179
LogP:	4.142
LogD:	2.39
LogS:	-3.734
# Rotatable Bonds:	3
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	3.908
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.918
MDCK Permeability:	1.4947913768992294e-05
Pgp-inhibitor:	0.404
Pgp-substrate:	0.529
Human Intestinal Absorption (HIA):	0.394
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	97.75934600830078%
Volume Distribution (VD):	0.523
Pgp-substrate:	3.761423110961914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.492
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.746
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.274
CYP3A4-substrate:	0.897

ADMET: Excretion

Clearance (CL):	8.453
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.797
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.217
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.426
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.874
Respiratory Toxicity:	0.099

Download Data

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

Natural Product: NPC474310

Natural Product ID:	NPC474310
*Common Name:**	Annulin B
IUPAC Name:	methyl 8-ethyl-9-hydroxy-2,4,4,7-tetramethyl-3,5,10-trioxo-4a,10a-dihydrobenzo[g]chromene-2-carboxylate
Synonyms:
Standard InCHIKey:	OHWPXNCKGWEEQM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O7/c1-7-10-9(2)8-11-12(14(10)22)16(24)17-13(15(11)23)20(3,4)18(25)21(5,28-17)19(26)27-6/h8,13,17,22H,7H2,1-6H3
SMILES:	CCC1=C(C2=C(C=C1C)C(=O)C3C(C2=O)OC(C(=O)C3(C)C)(C)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465020
PubChem CID:	44559102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO2240	Garveia annulata	Species	Bougainvilliidae	Eukaryota	n.a.	Northeastern Pacific	n.a.	PMID[17067170]
NPO2240	Garveia annulata	Species	Bougainvilliidae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	Ki	=	120.0	nM	PMID[553380]

☑ 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 NPC474310 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	329
0.1-0.2	1360
0.2-0.3	2742
0.3-0.4	6487
0.4-0.5	11353
0.5-0.6	7893
0.6-0.7	8593
0.7-0.8	3774
0.8-0.85	153
0.85-0.9	12
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8993	High Similarity	NPC94781
0.8951	High Similarity	NPC474311
0.8933	High Similarity	NPC120171
0.8808	High Similarity	NPC280753
0.8808	High Similarity	NPC44378
0.88	High Similarity	NPC5568
0.863	High Similarity	NPC475957
0.8618	High Similarity	NPC470479
0.8609	High Similarity	NPC136878
0.86	High Similarity	NPC29932
0.8571	High Similarity	NPC205918
0.8562	High Similarity	NPC472308
0.8481	Intermediate Similarity	NPC314795
0.8477	Intermediate Similarity	NPC79627
0.8467	Intermediate Similarity	NPC308572
0.8462	Intermediate Similarity	NPC312482
0.8456	Intermediate Similarity	NPC315578
0.8425	Intermediate Similarity	NPC202225
0.8421	Intermediate Similarity	NPC474630
0.8389	Intermediate Similarity	NPC114620
0.8389	Intermediate Similarity	NPC103337
0.8389	Intermediate Similarity	NPC26924
0.8387	Intermediate Similarity	NPC315520
0.8356	Intermediate Similarity	NPC78307
0.8354	Intermediate Similarity	NPC478027
0.8354	Intermediate Similarity	NPC474861
0.8322	Intermediate Similarity	NPC4214
0.8322	Intermediate Similarity	NPC173980
0.8301	Intermediate Similarity	NPC474309
0.8301	Intermediate Similarity	NPC475923
0.8293	Intermediate Similarity	NPC175477
0.8291	Intermediate Similarity	NPC471456
0.8289	Intermediate Similarity	NPC143898
0.8289	Intermediate Similarity	NPC66593
0.8276	Intermediate Similarity	NPC198305
0.8276	Intermediate Similarity	NPC108129
0.8255	Intermediate Similarity	NPC471452
0.8247	Intermediate Similarity	NPC63918
0.8247	Intermediate Similarity	NPC143685
0.8247	Intermediate Similarity	NPC285122
0.8247	Intermediate Similarity	NPC314437
0.8243	Intermediate Similarity	NPC80035
0.8239	Intermediate Similarity	NPC474360
0.8231	Intermediate Similarity	NPC254603
0.8231	Intermediate Similarity	NPC171968
0.8231	Intermediate Similarity	NPC477139
0.8228	Intermediate Similarity	NPC470408
0.8228	Intermediate Similarity	NPC218870
0.8228	Intermediate Similarity	NPC182921
0.8228	Intermediate Similarity	NPC472211
0.8228	Intermediate Similarity	NPC474824
0.8224	Intermediate Similarity	NPC248068
0.8219	Intermediate Similarity	NPC17083
0.8219	Intermediate Similarity	NPC471851
0.8207	Intermediate Similarity	NPC171460
0.8193	Intermediate Similarity	NPC473113
0.8188	Intermediate Similarity	NPC86524
0.8187	Intermediate Similarity	NPC317580
0.8182	Intermediate Similarity	NPC170055
0.8182	Intermediate Similarity	NPC478160
0.8176	Intermediate Similarity	NPC288089
0.8176	Intermediate Similarity	NPC3449
0.8153	Intermediate Similarity	NPC470037
0.8141	Intermediate Similarity	NPC112816
0.8141	Intermediate Similarity	NPC132810
0.8137	Intermediate Similarity	NPC326084
0.8133	Intermediate Similarity	NPC478021
0.8129	Intermediate Similarity	NPC471970
0.8129	Intermediate Similarity	NPC147250
0.8129	Intermediate Similarity	NPC120536
0.8117	Intermediate Similarity	NPC471906
0.8117	Intermediate Similarity	NPC218866
0.8117	Intermediate Similarity	NPC84568
0.8117	Intermediate Similarity	NPC300684
0.8117	Intermediate Similarity	NPC103910
0.8117	Intermediate Similarity	NPC48130
0.8113	Intermediate Similarity	NPC205172
0.8113	Intermediate Similarity	NPC474621
0.8113	Intermediate Similarity	NPC474622
0.8113	Intermediate Similarity	NPC209393
0.8108	Intermediate Similarity	NPC115458
0.8108	Intermediate Similarity	NPC52407
0.8105	Intermediate Similarity	NPC474300
0.8095	Intermediate Similarity	NPC70862
0.8092	Intermediate Similarity	NPC37992
0.8092	Intermediate Similarity	NPC327916
0.8092	Intermediate Similarity	NPC220496
0.8092	Intermediate Similarity	NPC42262
0.8092	Intermediate Similarity	NPC241349
0.8092	Intermediate Similarity	NPC32749
0.8092	Intermediate Similarity	NPC3218
0.8092	Intermediate Similarity	NPC471853
0.8092	Intermediate Similarity	NPC147542
0.8086	Intermediate Similarity	NPC475449
0.8084	Intermediate Similarity	NPC294501
0.8084	Intermediate Similarity	NPC183441
0.8079	Intermediate Similarity	NPC230811
0.8079	Intermediate Similarity	NPC13715
0.8077	Intermediate Similarity	NPC478018
0.8077	Intermediate Similarity	NPC119767
0.8075	Intermediate Similarity	NPC29552
0.8075	Intermediate Similarity	NPC206641
0.8075	Intermediate Similarity	NPC208651
0.8075	Intermediate Similarity	NPC67197
0.8069	Intermediate Similarity	NPC176130
0.8069	Intermediate Similarity	NPC51448
0.8069	Intermediate Similarity	NPC84672
0.8069	Intermediate Similarity	NPC115797
0.8069	Intermediate Similarity	NPC69424
0.8069	Intermediate Similarity	NPC72667
0.8069	Intermediate Similarity	NPC78364
0.8067	Intermediate Similarity	NPC315275
0.8067	Intermediate Similarity	NPC272268
0.8065	Intermediate Similarity	NPC470038
0.8063	Intermediate Similarity	NPC314257
0.8063	Intermediate Similarity	NPC266469
0.8063	Intermediate Similarity	NPC192219
0.8063	Intermediate Similarity	NPC82190
0.8063	Intermediate Similarity	NPC478221
0.8063	Intermediate Similarity	NPC318270
0.8063	Intermediate Similarity	NPC174599
0.8056	Intermediate Similarity	NPC287473
0.8052	Intermediate Similarity	NPC354984
0.8052	Intermediate Similarity	NPC476473
0.8052	Intermediate Similarity	NPC478164
0.8052	Intermediate Similarity	NPC21873
0.8052	Intermediate Similarity	NPC100242
0.805	Intermediate Similarity	NPC474534
0.805	Intermediate Similarity	NPC474533
0.8042	Intermediate Similarity	NPC275145
0.8041	Intermediate Similarity	NPC309430
0.8039	Intermediate Similarity	NPC272907
0.8039	Intermediate Similarity	NPC257003
0.8039	Intermediate Similarity	NPC2681
0.8039	Intermediate Similarity	NPC290550
0.8036	Intermediate Similarity	NPC65118
0.8027	Intermediate Similarity	NPC199253
0.8027	Intermediate Similarity	NPC136588
0.8026	Intermediate Similarity	NPC476477
0.8026	Intermediate Similarity	NPC299405
0.8026	Intermediate Similarity	NPC306835
0.8026	Intermediate Similarity	NPC29771
0.8026	Intermediate Similarity	NPC216312
0.8026	Intermediate Similarity	NPC295339
0.8026	Intermediate Similarity	NPC471602
0.8026	Intermediate Similarity	NPC256463
0.8026	Intermediate Similarity	NPC111422
0.8025	Intermediate Similarity	NPC264229
0.8025	Intermediate Similarity	NPC473719
0.8025	Intermediate Similarity	NPC46549
0.8024	Intermediate Similarity	NPC313717
0.8024	Intermediate Similarity	NPC315306
0.8024	Intermediate Similarity	NPC470580
0.8014	Intermediate Similarity	NPC3009
0.8014	Intermediate Similarity	NPC237225
0.8013	Intermediate Similarity	NPC470570
0.8013	Intermediate Similarity	NPC273798
0.8013	Intermediate Similarity	NPC51513
0.8013	Intermediate Similarity	NPC202112
0.8012	Intermediate Similarity	NPC471295
0.8012	Intermediate Similarity	NPC471968
0.8012	Intermediate Similarity	NPC283480
0.8012	Intermediate Similarity	NPC107009
0.8012	Intermediate Similarity	NPC148323
0.8	Intermediate Similarity	NPC478026
0.8	Intermediate Similarity	NPC316262
0.8	Intermediate Similarity	NPC254492
0.8	Intermediate Similarity	NPC144247
0.8	Intermediate Similarity	NPC478231
0.8	Intermediate Similarity	NPC469375
0.8	Intermediate Similarity	NPC294679
0.8	Intermediate Similarity	NPC329647
0.8	Intermediate Similarity	NPC469854
0.8	Intermediate Similarity	NPC470735
0.8	Intermediate Similarity	NPC145301
0.8	Intermediate Similarity	NPC314653
0.8	Intermediate Similarity	NPC469856
0.8	Intermediate Similarity	NPC8493
0.8	Intermediate Similarity	NPC126707
0.8	Intermediate Similarity	NPC244691
0.7988	Intermediate Similarity	NPC315772
0.7987	Intermediate Similarity	NPC469855
0.7987	Intermediate Similarity	NPC53896
0.7987	Intermediate Similarity	NPC30846
0.7987	Intermediate Similarity	NPC471972
0.7987	Intermediate Similarity	NPC471971
0.7987	Intermediate Similarity	NPC49742
0.7987	Intermediate Similarity	NPC111845
0.7987	Intermediate Similarity	NPC135524
0.7987	Intermediate Similarity	NPC59459
0.7987	Intermediate Similarity	NPC193169
0.7987	Intermediate Similarity	NPC193555
0.7987	Intermediate Similarity	NPC43627
0.7987	Intermediate Similarity	NPC138472
0.7986	Intermediate Similarity	NPC68756
0.7986	Intermediate Similarity	NPC152525
0.7976	Intermediate Similarity	NPC270027
0.7965	Intermediate Similarity	NPC475148
0.7965	Intermediate Similarity	NPC475656
0.7964	Intermediate Similarity	NPC473096

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 NPC474310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	894
0.2-0.3	1593
0.3-0.4	2739
0.4-0.5	2135
0.5-0.6	1036
0.6-0.7	407
0.7-0.8	67
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
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.775	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8150	Discontinued
0.7568	Intermediate Similarity	NPD1470	Approved
0.7548	Intermediate Similarity	NPD5405	Approved
0.7548	Intermediate Similarity	NPD5404	Approved
0.7548	Intermediate Similarity	NPD5408	Approved
0.7548	Intermediate Similarity	NPD5406	Approved
0.753	Intermediate Similarity	NPD7075	Discontinued
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6232	Discontinued
0.7455	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7458	Discontinued
0.7381	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6599	Discontinued
0.7375	Intermediate Similarity	NPD3300	Phase 2
0.7375	Intermediate Similarity	NPD7236	Approved
0.7366	Intermediate Similarity	NPD8319	Approved
0.7366	Intermediate Similarity	NPD8320	Phase 1
0.7349	Intermediate Similarity	NPD7819	Suspended
0.7348	Intermediate Similarity	NPD6534	Approved
0.7348	Intermediate Similarity	NPD6535	Approved
0.7329	Intermediate Similarity	NPD7390	Discontinued
0.7325	Intermediate Similarity	NPD2935	Discontinued
0.7312	Intermediate Similarity	NPD7435	Discontinued
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7297	Intermediate Similarity	NPD1201	Approved
0.7278	Intermediate Similarity	NPD1471	Phase 3
0.7273	Intermediate Similarity	NPD6663	Approved
0.7261	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2799	Discontinued
0.7256	Intermediate Similarity	NPD7239	Suspended
0.7255	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7003	Approved
0.725	Intermediate Similarity	NPD4628	Phase 3
0.725	Intermediate Similarity	NPD8166	Discontinued
0.7241	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5736	Approved
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7228	Intermediate Similarity	NPD7700	Phase 2
0.7228	Intermediate Similarity	NPD7699	Phase 2
0.7212	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2313	Discontinued
0.7193	Intermediate Similarity	NPD6959	Discontinued
0.7188	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6801	Discontinued
0.7169	Intermediate Similarity	NPD4380	Phase 2
0.7161	Intermediate Similarity	NPD7961	Discontinued
0.7151	Intermediate Similarity	NPD6781	Approved
0.7151	Intermediate Similarity	NPD6782	Approved
0.7151	Intermediate Similarity	NPD6780	Approved
0.7151	Intermediate Similarity	NPD6779	Approved
0.7151	Intermediate Similarity	NPD6778	Approved
0.7151	Intermediate Similarity	NPD6777	Approved
0.7151	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7127	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7411	Suspended
0.7125	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7103	Intermediate Similarity	NPD5951	Approved
0.7103	Intermediate Similarity	NPD2629	Approved
0.7101	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6190	Approved
0.7083	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7874	Approved
0.7073	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5710	Approved
0.7052	Intermediate Similarity	NPD5711	Approved
0.7047	Intermediate Similarity	NPD2932	Approved
0.7047	Intermediate Similarity	NPD3019	Approved
0.7044	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7696	Phase 3
0.7037	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7697	Approved
0.7037	Intermediate Similarity	NPD7698	Approved
0.703	Intermediate Similarity	NPD6273	Approved
0.7012	Intermediate Similarity	NPD6799	Approved
0.7011	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6213	Phase 3
0.7011	Intermediate Similarity	NPD6212	Phase 3
0.7	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD5402	Approved
0.7	Intermediate Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD1164	Approved
0.6989	Remote Similarity	NPD7799	Discontinued
0.6987	Remote Similarity	NPD3764	Approved
0.6982	Remote Similarity	NPD1934	Approved
0.6971	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3882	Suspended
0.6957	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2344	Approved
0.6949	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5494	Approved
0.6933	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6765	Approved
0.6927	Remote Similarity	NPD6559	Discontinued
0.6927	Remote Similarity	NPD6764	Approved
0.6923	Remote Similarity	NPD7008	Discontinued
0.6899	Remote Similarity	NPD943	Approved
0.6894	Remote Similarity	NPD6099	Approved
0.6894	Remote Similarity	NPD6100	Approved
0.6893	Remote Similarity	NPD3751	Discontinued
0.6891	Remote Similarity	NPD7701	Phase 2
0.6889	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6166	Phase 2
0.6875	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7801	Approved
0.6871	Remote Similarity	NPD2800	Approved
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7057	Phase 3
0.686	Remote Similarity	NPD7058	Phase 2
0.6855	Remote Similarity	NPD6355	Discontinued
0.6839	Remote Similarity	NPD2798	Approved
0.6833	Remote Similarity	NPD8368	Discontinued
0.6825	Remote Similarity	NPD8285	Discontinued
0.6824	Remote Similarity	NPD4198	Discontinued
0.6821	Remote Similarity	NPD3749	Approved
0.6821	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1283	Approved
0.681	Remote Similarity	NPD1549	Phase 2
0.6798	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3972	Approved
0.6796	Remote Similarity	NPD4954	Approved
0.6796	Remote Similarity	NPD5028	Approved
0.6796	Remote Similarity	NPD5034	Approved
0.6796	Remote Similarity	NPD36	Approved
0.6796	Remote Similarity	NPD4955	Approved
0.6796	Remote Similarity	NPD5026	Approved
0.6792	Remote Similarity	NPD2979	Phase 3
0.6792	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2438	Suspended
0.6788	Remote Similarity	NPD2309	Approved
0.6786	Remote Similarity	NPD5403	Approved
0.6779	Remote Similarity	NPD9493	Approved
0.6778	Remote Similarity	NPD6797	Phase 2
0.6778	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6784	Approved
0.6776	Remote Similarity	NPD6785	Approved
0.6772	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD7985	Registered
0.6772	Remote Similarity	NPD3268	Approved
0.6769	Remote Similarity	NPD8151	Discontinued
0.6766	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.675	Remote Similarity	NPD447	Suspended
0.675	Remote Similarity	NPD230	Phase 1
0.6748	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2801	Approved
0.674	Remote Similarity	NPD7251	Discontinued
0.674	Remote Similarity	NPD5030	Phase 2
0.6733	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1510	Phase 2
0.6726	Remote Similarity	NPD5049	Phase 3
0.6721	Remote Similarity	NPD8407	Phase 2
0.6712	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3317	Approved
0.6711	Remote Similarity	NPD4626	Approved
0.6709	Remote Similarity	NPD7095	Approved
0.6708	Remote Similarity	NPD1607	Approved
0.6708	Remote Similarity	NPD6651	Approved
0.6705	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3818	Discontinued
0.6703	Remote Similarity	NPD7808	Phase 3
0.669	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD9545	Approved
0.6687	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD3026	Approved
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD5035	Approved
0.6667	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD7768	Phase 2
0.6649	Remote Similarity	NPD5038	Approved
0.6649	Remote Similarity	NPD5037	Approved
0.6647	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD5762	Approved
0.6646	Remote Similarity	NPD5763	Approved
0.6645	Remote Similarity	NPD3024	Approved
0.6645	Remote Similarity	NPD3025	Approved
0.6645	Remote Similarity	NPD5691	Approved
0.6632	Remote Similarity	NPD6823	Phase 2
0.663	Remote Similarity	NPD7074	Phase 3
0.6627	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3750	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