NPASS Compound

Structure

NPC172154 OpenBabel07101719252D 34 39 0 0 1 0 0 0 0 0999 V2000 -7.1527 2.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7707 4.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 4.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 3.4135 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 3.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 3.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 4.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 3.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 3.9680 0.0000 C 0 0 2 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 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1235 5.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1369 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 6.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 4.9190 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 28 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 14 25 1 0 0 0 0 15 22 2 0 0 0 0 16 21 1 0 0 0 0 16 27 1 6 0 0 0 17 21 1 0 0 0 0 17 26 1 6 0 0 0 18 22 1 0 0 0 0 18 29 1 6 0 0 0 19 15 1 1 0 0 0 19 33 1 0 0 0 0 20 27 1 0 0 0 0 20 30 2 0 0 0 0 21 23 1 0 0 0 0 22 26 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 28 1 0 0 0 0 24 34 1 0 0 0 0 25 31 2 0 0 0 0 25 33 1 0 0 0 0 27 28 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.25
Volume:	481.064
LogP:	3.093
LogD:	3.123
LogS:	-4.315
# Rotatable Bonds:	1
TPSA:	96.36
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	5.785
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.843
MDCK Permeability:	1.7741353076417e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	61.5772590637207%
Volume Distribution (VD):	1.413
Pgp-substrate:	29.032594680786133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.347
CYP2C19-substrate:	0.774
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.629

ADMET: Excretion

Clearance (CL):	10.283
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.396
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.291
Carcinogencity:	0.921
Eye Corrosion:	0.037
Eye Irritation:	0.034
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC172154

Natural Product ID:	NPC172154
*Common Name:**	Exodeconolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YARITIRBZOEIHO-PLYJTDRGSA-N
Standard InCHI:	InChI=1S/C28H36O6/c1-13-11-19(33-25(31)14(13)2)15(3)22-18(29)12-17-21-16(8-10-26(17,22)4)27(5)20(30)7-6-9-28(27,32)24-23(21)34-24/h6-7,16-19,21,23-24,29,32H,8-12H2,1-5H3/b22-15+/t16-,17-,18-,19+,21+,23-,24-,26-,27-,28-/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)/C(=C/1[C@H](C[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)C(=O)C=CC[C@@]1([C@@H]1[C@H]3O1)O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465497
PubChem CID:	44566977
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO32637	exodeconus maritimus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]

☑ 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	1
Others	3

Activity Type	# Activity
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CQ	>	42.7	uM	PMID[467931]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	15.8	uM	PMID[467931]
NPT2	Others	Unspecified		Ratio	>	2.7	n.a.	PMID[467931]
NPT27	Others	Unspecified		IC50	>	42700.0	nM	PMID[467931]

☑ 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 NPC172154 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	253
0.1-0.2	1413
0.2-0.3	3917
0.3-0.4	6852
0.4-0.5	11722
0.5-0.6	8860
0.6-0.7	6489
0.7-0.8	2709
0.8-0.85	338
0.85-0.9	94
0.9-0.95	41
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC81736
0.9741	High Similarity	NPC293112
0.9739	High Similarity	NPC11895
0.9652	High Similarity	NPC170538
0.9569	High Similarity	NPC469789
0.9487	High Similarity	NPC8369
0.9407	High Similarity	NPC473635
0.9397	High Similarity	NPC67569
0.9386	High Similarity	NPC470492
0.9316	High Similarity	NPC23786
0.9316	High Similarity	NPC470265
0.9224	High Similarity	NPC264954
0.9217	High Similarity	NPC20302
0.9217	High Similarity	NPC286528
0.9217	High Similarity	NPC140055
0.9217	High Similarity	NPC167606
0.916	High Similarity	NPC8374
0.9153	High Similarity	NPC269642
0.9145	High Similarity	NPC154491
0.9145	High Similarity	NPC474370
0.9145	High Similarity	NPC268530
0.9138	High Similarity	NPC709
0.9138	High Similarity	NPC50774
0.9068	High Similarity	NPC46570
0.9068	High Similarity	NPC4021
0.9068	High Similarity	NPC159456
0.906	High Similarity	NPC475041
0.9052	High Similarity	NPC312824
0.9052	High Similarity	NPC469684
0.9052	High Similarity	NPC183580
0.9052	High Similarity	NPC470493
0.9043	High Similarity	NPC67259
0.9043	High Similarity	NPC147912
0.9016	High Similarity	NPC231529
0.8992	High Similarity	NPC107493
0.8992	High Similarity	NPC88326
0.8992	High Similarity	NPC153700
0.8983	High Similarity	NPC251226
0.8983	High Similarity	NPC476961
0.8974	High Similarity	NPC329736
0.8974	High Similarity	NPC186525
0.8966	High Similarity	NPC270929
0.8957	High Similarity	NPC122056
0.8917	High Similarity	NPC204812
0.8917	High Similarity	NPC120724
0.8898	High Similarity	NPC230513
0.8898	High Similarity	NPC61520
0.8898	High Similarity	NPC475520
0.8898	High Similarity	NPC476960
0.8898	High Similarity	NPC42673
0.8879	High Similarity	NPC284915
0.8862	High Similarity	NPC473593
0.8852	High Similarity	NPC287423
0.8852	High Similarity	NPC473253
0.8843	High Similarity	NPC241456
0.8843	High Similarity	NPC469790
0.8843	High Similarity	NPC32868
0.8814	High Similarity	NPC284707
0.8803	High Similarity	NPC64318
0.877	High Similarity	NPC120994
0.877	High Similarity	NPC203702
0.876	High Similarity	NPC473979
0.875	High Similarity	NPC473256
0.875	High Similarity	NPC470878
0.8739	High Similarity	NPC473274
0.8729	High Similarity	NPC476965
0.8729	High Similarity	NPC55296
0.8729	High Similarity	NPC53396
0.8729	High Similarity	NPC58662
0.8729	High Similarity	NPC98249
0.8729	High Similarity	NPC470959
0.872	High Similarity	NPC231240
0.871	High Similarity	NPC470880
0.8707	High Similarity	NPC269530
0.8699	High Similarity	NPC470882
0.8689	High Similarity	NPC470494
0.8689	High Similarity	NPC3381
0.8667	High Similarity	NPC79579
0.8667	High Similarity	NPC476962
0.8655	High Similarity	NPC153440
0.8655	High Similarity	NPC473720
0.8651	High Similarity	NPC316915
0.8644	High Similarity	NPC176840
0.8644	High Similarity	NPC190286
0.8632	High Similarity	NPC25909
0.8632	High Similarity	NPC317210
0.8629	High Similarity	NPC473620
0.8621	High Similarity	NPC474846
0.8621	High Similarity	NPC469656
0.8621	High Similarity	NPC474229
0.8621	High Similarity	NPC469655
0.8607	High Similarity	NPC67251
0.8595	High Similarity	NPC310511
0.8583	High Similarity	NPC473203
0.8583	High Similarity	NPC473636
0.8583	High Similarity	NPC5292
0.8583	High Similarity	NPC473270
0.8583	High Similarity	NPC77689
0.8571	High Similarity	NPC243065
0.8571	High Similarity	NPC134430
0.856	High Similarity	NPC476966
0.8559	High Similarity	NPC474181
0.8559	High Similarity	NPC238667
0.8548	High Similarity	NPC473265
0.8547	High Similarity	NPC191620
0.8547	High Similarity	NPC236217
0.8537	High Similarity	NPC24651
0.8537	High Similarity	NPC470922
0.8537	High Similarity	NPC476729
0.8534	High Similarity	NPC472215
0.8534	High Similarity	NPC253906
0.8534	High Similarity	NPC37116
0.8534	High Similarity	NPC76084
0.8534	High Similarity	NPC472214
0.8512	High Similarity	NPC474585
0.85	High Similarity	NPC478206
0.85	High Similarity	NPC478205
0.85	High Similarity	NPC108581
0.85	High Similarity	NPC251310
0.85	High Similarity	NPC257457
0.85	High Similarity	NPC311554
0.8475	Intermediate Similarity	NPC962
0.8475	Intermediate Similarity	NPC250109
0.8462	Intermediate Similarity	NPC474315
0.8462	Intermediate Similarity	NPC470961
0.8455	Intermediate Similarity	NPC105926
0.8455	Intermediate Similarity	NPC265557
0.8455	Intermediate Similarity	NPC18945
0.8455	Intermediate Similarity	NPC91693
0.8448	Intermediate Similarity	NPC469370
0.843	Intermediate Similarity	NPC305260
0.843	Intermediate Similarity	NPC472667
0.843	Intermediate Similarity	NPC211093
0.843	Intermediate Similarity	NPC473839
0.843	Intermediate Similarity	NPC270850
0.8425	Intermediate Similarity	NPC471855
0.8417	Intermediate Similarity	NPC474518
0.8417	Intermediate Similarity	NPC13713
0.8417	Intermediate Similarity	NPC471854
0.8417	Intermediate Similarity	NPC475809
0.8417	Intermediate Similarity	NPC478204
0.8417	Intermediate Similarity	NPC284068
0.8417	Intermediate Similarity	NPC239273
0.8417	Intermediate Similarity	NPC473968
0.8403	Intermediate Similarity	NPC470953
0.8403	Intermediate Similarity	NPC117712
0.84	Intermediate Similarity	NPC42399
0.839	Intermediate Similarity	NPC476163
0.839	Intermediate Similarity	NPC476801
0.839	Intermediate Similarity	NPC90952
0.839	Intermediate Similarity	NPC472002
0.839	Intermediate Similarity	NPC277769
0.8387	Intermediate Similarity	NPC473919
0.8387	Intermediate Similarity	NPC473709
0.8387	Intermediate Similarity	NPC473255
0.8376	Intermediate Similarity	NPC29133
0.8374	Intermediate Similarity	NPC222688
0.8374	Intermediate Similarity	NPC312833
0.8347	Intermediate Similarity	NPC113448
0.8346	Intermediate Similarity	NPC173347
0.8346	Intermediate Similarity	NPC220757
0.8346	Intermediate Similarity	NPC196921
0.8333	Intermediate Similarity	NPC148458
0.8333	Intermediate Similarity	NPC245094
0.8333	Intermediate Similarity	NPC266728
0.8333	Intermediate Similarity	NPC179626
0.8333	Intermediate Similarity	NPC49492
0.8333	Intermediate Similarity	NPC470075
0.8333	Intermediate Similarity	NPC311534
0.832	Intermediate Similarity	NPC225049
0.8319	Intermediate Similarity	NPC477126
0.8306	Intermediate Similarity	NPC473802
0.8306	Intermediate Similarity	NPC472399
0.8306	Intermediate Similarity	NPC55602
0.8305	Intermediate Similarity	NPC470960
0.8305	Intermediate Similarity	NPC317107
0.8295	Intermediate Similarity	NPC476823
0.8293	Intermediate Similarity	NPC477046
0.8293	Intermediate Similarity	NPC102822
0.8293	Intermediate Similarity	NPC470779
0.8291	Intermediate Similarity	NPC5475
0.8291	Intermediate Similarity	NPC472216
0.8291	Intermediate Similarity	NPC173905
0.8291	Intermediate Similarity	NPC284828
0.8291	Intermediate Similarity	NPC475065
0.8281	Intermediate Similarity	NPC476193
0.8279	Intermediate Similarity	NPC475775
0.8279	Intermediate Similarity	NPC476529
0.8276	Intermediate Similarity	NPC67321
0.8276	Intermediate Similarity	NPC180744
0.8276	Intermediate Similarity	NPC477916
0.8276	Intermediate Similarity	NPC329048
0.8276	Intermediate Similarity	NPC187435
0.8276	Intermediate Similarity	NPC330011
0.8276	Intermediate Similarity	NPC91034
0.8268	Intermediate Similarity	NPC175186
0.8268	Intermediate Similarity	NPC35109
0.8268	Intermediate Similarity	NPC221414
0.8268	Intermediate Similarity	NPC104382
0.8268	Intermediate Similarity	NPC471407

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 NPC172154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1562
0.2-0.3	3572
0.3-0.4	2423
0.4-0.5	771
0.5-0.6	336
0.6-0.7	167
0.7-0.8	93
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9217	High Similarity	NPD7115	Discovery
0.8065	Intermediate Similarity	NPD6319	Approved
0.7984	Intermediate Similarity	NPD7319	Approved
0.7983	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD7639	Approved
0.7913	Intermediate Similarity	NPD7640	Approved
0.7899	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD4632	Approved
0.7826	Intermediate Similarity	NPD7638	Approved
0.7826	Intermediate Similarity	NPD4225	Approved
0.7812	Intermediate Similarity	NPD7492	Approved
0.7787	Intermediate Similarity	NPD8297	Approved
0.7778	Intermediate Similarity	NPD6054	Approved
0.7769	Intermediate Similarity	NPD7736	Approved
0.7769	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD6616	Approved
0.7752	Intermediate Similarity	NPD7507	Approved
0.775	Intermediate Similarity	NPD6881	Approved
0.775	Intermediate Similarity	NPD6899	Approved
0.7731	Intermediate Similarity	NPD6008	Approved
0.7705	Intermediate Similarity	NPD6649	Approved
0.7705	Intermediate Similarity	NPD6650	Approved
0.7692	Intermediate Similarity	NPD7078	Approved
0.7667	Intermediate Similarity	NPD5697	Approved
0.7656	Intermediate Similarity	NPD6370	Approved
0.7623	Intermediate Similarity	NPD7102	Approved
0.7623	Intermediate Similarity	NPD4634	Approved
0.7623	Intermediate Similarity	NPD7290	Approved
0.7623	Intermediate Similarity	NPD6883	Approved
0.7597	Intermediate Similarity	NPD7604	Phase 2
0.7583	Intermediate Similarity	NPD6402	Approved
0.7583	Intermediate Similarity	NPD5739	Approved
0.7583	Intermediate Similarity	NPD6675	Approved
0.7583	Intermediate Similarity	NPD7128	Approved
0.7578	Intermediate Similarity	NPD6015	Approved
0.7578	Intermediate Similarity	NPD6016	Approved
0.7561	Intermediate Similarity	NPD6847	Approved
0.7561	Intermediate Similarity	NPD6869	Approved
0.7561	Intermediate Similarity	NPD8130	Phase 1
0.7561	Intermediate Similarity	NPD6617	Approved
0.7542	Intermediate Similarity	NPD5344	Discontinued
0.7541	Intermediate Similarity	NPD6013	Approved
0.7541	Intermediate Similarity	NPD6012	Approved
0.7541	Intermediate Similarity	NPD6014	Approved
0.7541	Intermediate Similarity	NPD6372	Approved
0.7541	Intermediate Similarity	NPD6373	Approved
0.754	Intermediate Similarity	NPD6009	Approved
0.7521	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5988	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.748	Intermediate Similarity	NPD6371	Approved
0.7479	Intermediate Similarity	NPD5211	Phase 2
0.7459	Intermediate Similarity	NPD7320	Approved
0.7459	Intermediate Similarity	NPD6011	Approved
0.7442	Intermediate Similarity	NPD7503	Approved
0.7442	Intermediate Similarity	NPD5983	Phase 2
0.7442	Intermediate Similarity	NPD8513	Phase 3
0.7424	Intermediate Similarity	NPD8293	Discontinued
0.7422	Intermediate Similarity	NPD7516	Approved
0.7377	Intermediate Similarity	NPD5701	Approved
0.7377	Intermediate Similarity	NPD6412	Phase 2
0.736	Intermediate Similarity	NPD6053	Discontinued
0.7355	Intermediate Similarity	NPD5141	Approved
0.7348	Intermediate Similarity	NPD6336	Discontinued
0.7344	Intermediate Similarity	NPD7327	Approved
0.7344	Intermediate Similarity	NPD7328	Approved
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.7328	Intermediate Similarity	NPD8328	Phase 3
0.7317	Intermediate Similarity	NPD6686	Approved
0.7311	Intermediate Similarity	NPD5286	Approved
0.7311	Intermediate Similarity	NPD4696	Approved
0.7311	Intermediate Similarity	NPD5285	Approved
0.7308	Intermediate Similarity	NPD8515	Approved
0.7308	Intermediate Similarity	NPD8516	Approved
0.7308	Intermediate Similarity	NPD8517	Approved
0.7304	Intermediate Similarity	NPD6079	Approved
0.7217	Intermediate Similarity	NPD5785	Approved
0.719	Intermediate Similarity	NPD5225	Approved
0.719	Intermediate Similarity	NPD5226	Approved
0.719	Intermediate Similarity	NPD4633	Approved
0.719	Intermediate Similarity	NPD5224	Approved
0.7176	Intermediate Similarity	NPD8379	Approved
0.7176	Intermediate Similarity	NPD8296	Approved
0.7176	Intermediate Similarity	NPD6921	Approved
0.7176	Intermediate Similarity	NPD8378	Approved
0.7176	Intermediate Similarity	NPD8380	Approved
0.7176	Intermediate Similarity	NPD8335	Approved
0.7176	Intermediate Similarity	NPD8033	Approved
0.7167	Intermediate Similarity	NPD6648	Approved
0.7154	Intermediate Similarity	NPD7101	Approved
0.7154	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5175	Approved
0.7131	Intermediate Similarity	NPD5174	Approved
0.713	Intermediate Similarity	NPD5328	Approved
0.7107	Intermediate Similarity	NPD5223	Approved
0.7099	Intermediate Similarity	NPD8294	Approved
0.7099	Intermediate Similarity	NPD8377	Approved
0.7094	Intermediate Similarity	NPD5778	Approved
0.7094	Intermediate Similarity	NPD6399	Phase 3
0.7094	Intermediate Similarity	NPD5779	Approved
0.7077	Intermediate Similarity	NPD6335	Approved
0.7059	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5222	Approved
0.7059	Intermediate Similarity	NPD5221	Approved
0.7054	Intermediate Similarity	NPD6274	Approved
0.7034	Intermediate Similarity	NPD7748	Approved
0.7025	Intermediate Similarity	NPD4700	Approved
0.7018	Intermediate Similarity	NPD3618	Phase 1
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD6317	Approved
0.7	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6033	Approved
0.6984	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7260	Phase 2
0.6957	Remote Similarity	NPD3573	Approved
0.6947	Remote Similarity	NPD6314	Approved
0.6947	Remote Similarity	NPD6313	Approved
0.6942	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD46	Approved
0.6917	Remote Similarity	NPD4697	Phase 3
0.6917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8074	Phase 3
0.6905	Remote Similarity	NPD4729	Approved
0.6905	Remote Similarity	NPD4730	Approved
0.6899	Remote Similarity	NPD8133	Approved
0.6897	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5330	Approved
0.687	Remote Similarity	NPD7521	Approved
0.687	Remote Similarity	NPD6409	Approved
0.687	Remote Similarity	NPD7334	Approved
0.687	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7146	Approved
0.687	Remote Similarity	NPD6684	Approved
0.6864	Remote Similarity	NPD6411	Approved
0.6833	Remote Similarity	NPD4629	Approved
0.6833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5695	Phase 3
0.6833	Remote Similarity	NPD5210	Approved
0.6807	Remote Similarity	NPD4202	Approved
0.6797	Remote Similarity	NPD5250	Approved
0.6797	Remote Similarity	NPD5249	Phase 3
0.6797	Remote Similarity	NPD5251	Approved
0.6797	Remote Similarity	NPD5248	Approved
0.6797	Remote Similarity	NPD5247	Approved
0.6791	Remote Similarity	NPD6908	Approved
0.6791	Remote Similarity	NPD6909	Approved
0.6783	Remote Similarity	NPD5363	Approved
0.6783	Remote Similarity	NPD1694	Approved
0.6772	Remote Similarity	NPD5128	Approved
0.6752	Remote Similarity	NPD6903	Approved
0.675	Remote Similarity	NPD7900	Approved
0.675	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4767	Approved
0.6746	Remote Similarity	NPD4768	Approved
0.6744	Remote Similarity	NPD5216	Approved
0.6744	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5215	Approved
0.6744	Remote Similarity	NPD5217	Approved
0.6724	Remote Similarity	NPD5786	Approved
0.6723	Remote Similarity	NPD7983	Approved
0.6723	Remote Similarity	NPD5693	Phase 1
0.672	Remote Similarity	NPD4754	Approved
0.6696	Remote Similarity	NPD3665	Phase 1
0.6696	Remote Similarity	NPD3133	Approved
0.6696	Remote Similarity	NPD4786	Approved
0.6696	Remote Similarity	NPD3666	Approved
0.6695	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4753	Phase 2
0.6695	Remote Similarity	NPD6101	Approved
0.6694	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3667	Approved
0.6639	Remote Similarity	NPD7838	Discovery
0.6615	Remote Similarity	NPD5127	Approved
0.6612	Remote Similarity	NPD6001	Approved
0.661	Remote Similarity	NPD6672	Approved
0.661	Remote Similarity	NPD5737	Approved
0.6583	Remote Similarity	NPD5281	Approved
0.6583	Remote Similarity	NPD5284	Approved
0.6583	Remote Similarity	NPD8035	Phase 2
0.6583	Remote Similarity	NPD8034	Phase 2
0.6569	Remote Similarity	NPD6067	Discontinued
0.6556	Remote Similarity	NPD7236	Approved
0.6555	Remote Similarity	NPD6904	Approved
0.6555	Remote Similarity	NPD6673	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