NPASS Compound

Structure

CID220462 OpenBabel06191716012D 22 26 0 0 1 0 0 0 0 0999 V2000 -2.5199 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6803 -0.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3591 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6799 1.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6795 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6796 1.9399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0119 0.9690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3593 -0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8397 1.4549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8396 0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 1.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5191 0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5194 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8399 0.4849 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6800 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2403 -1.4769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8141 -0.4999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5192 1.4553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4419 1.7538 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4416 0.1843 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 2 1 0 0 0 0 1 8 1 0 0 0 0 2 16 1 0 0 0 0 3 8 1 0 0 0 0 3 14 2 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 7 21 1 0 0 0 0 8 17 2 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 6 1 1 0 0 0 10 15 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 1 0 0 0 15 22 1 0 0 0 0 16 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	282.069
LogP:	1.239
LogD:	1.529
LogS:	-3.774
# Rotatable Bonds:	0
TPSA:	74.22
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	4.264
Fsp3:	0.438
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:	-4.904
MDCK Permeability:	3.86257452191785e-05
Pgp-inhibitor:	0.05
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.607
Plasma Protein Binding (PPB):	89.88702392578125%
Volume Distribution (VD):	1.363
Pgp-substrate:	8.393729209899902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.923
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.361
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.475
CYP2D6-inhibitor:	0.729
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.864

ADMET: Excretion

Clearance (CL):	12.25
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.405
Drug-inuced Liver Injury (DILI):	0.19
AMES Toxicity:	0.878
Rat Oral Acute Toxicity:	0.437
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.252
Carcinogencity:	0.937
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.069

Download Data

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

Natural Product: NPC220462

Natural Product ID:	NPC220462
*Common Name:**	IFWVGNKYQITBOH-AMKSKSKJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IFWVGNKYQITBOH-AMKSKSKJSA-N
Standard InCHI:	InChI=1S/C16H14O6/c17-8-1-2-16(18)14(3-8)19-6-10-9-4-12-13(21-7-20-12)5-11(9)22-15(10)16/h3-5,10,15,18H,1-2,6-7H2/t10-,15+,16+/m0/s1
SMILES:	C1C[C@]2(C(=CC1=O)OC[C@H]1c3cc4c(cc3O[C@@H]21)OCO4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL240715
PubChem CID:	44437742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	stem	n.a.	PMID[17077549]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	stems	n.a.	n.a.	PMID[17158054]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100000.0	nM	PMID[479716]

☑ 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 NPC220462 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	404
0.1-0.2	1501
0.2-0.3	3339
0.3-0.4	7576
0.4-0.5	10565
0.5-0.6	4584
0.6-0.7	5646
0.7-0.8	7864
0.8-0.85	1167
0.85-0.9	50
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8994	High Similarity	NPC469575
0.8974	High Similarity	NPC42871
0.8974	High Similarity	NPC202249
0.8974	High Similarity	NPC188962
0.8938	High Similarity	NPC470178
0.8882	High Similarity	NPC212697
0.8773	High Similarity	NPC42892
0.8758	High Similarity	NPC226540
0.8758	High Similarity	NPC162193
0.8742	High Similarity	NPC474990
0.8727	High Similarity	NPC475825
0.8727	High Similarity	NPC223375
0.8712	High Similarity	NPC113093
0.8701	High Similarity	NPC30720
0.8696	High Similarity	NPC162668
0.8693	High Similarity	NPC178014
0.8693	High Similarity	NPC11422
0.8693	High Similarity	NPC42716
0.8693	High Similarity	NPC474749
0.8683	High Similarity	NPC156635
0.8654	High Similarity	NPC177830
0.8645	High Similarity	NPC166584
0.8645	High Similarity	NPC301961
0.8642	High Similarity	NPC478199
0.8625	High Similarity	NPC258644
0.8616	High Similarity	NPC18954
0.8599	High Similarity	NPC474975
0.8589	High Similarity	NPC94777
0.8589	High Similarity	NPC475985
0.8554	High Similarity	NPC212748
0.8535	High Similarity	NPC475170
0.8528	High Similarity	NPC41009
0.8528	High Similarity	NPC125991
0.8526	High Similarity	NPC71726
0.8521	High Similarity	NPC67302
0.8521	High Similarity	NPC29587
0.8519	High Similarity	NPC285973
0.8519	High Similarity	NPC225624
0.8512	High Similarity	NPC472607
0.8509	High Similarity	NPC469584
0.8509	High Similarity	NPC167595
0.8494	Intermediate Similarity	NPC112755
0.8494	Intermediate Similarity	NPC170675
0.8494	Intermediate Similarity	NPC472381
0.8494	Intermediate Similarity	NPC471457
0.8494	Intermediate Similarity	NPC472383
0.8485	Intermediate Similarity	NPC181616
0.8485	Intermediate Similarity	NPC173292
0.8485	Intermediate Similarity	NPC99957
0.8485	Intermediate Similarity	NPC170245
0.848	Intermediate Similarity	NPC473883
0.8476	Intermediate Similarity	NPC475865
0.8476	Intermediate Similarity	NPC110257
0.8476	Intermediate Similarity	NPC273959
0.8471	Intermediate Similarity	NPC236089
0.8471	Intermediate Similarity	NPC240521
0.8466	Intermediate Similarity	NPC295009
0.8466	Intermediate Similarity	NPC260640
0.8462	Intermediate Similarity	NPC257714
0.8457	Intermediate Similarity	NPC215375
0.8457	Intermediate Similarity	NPC472565
0.8457	Intermediate Similarity	NPC62518
0.8452	Intermediate Similarity	NPC307466
0.8447	Intermediate Similarity	NPC235165
0.8447	Intermediate Similarity	NPC255106
0.8443	Intermediate Similarity	NPC22195
0.8443	Intermediate Similarity	NPC224462
0.8443	Intermediate Similarity	NPC21190
0.8443	Intermediate Similarity	NPC34287
0.8443	Intermediate Similarity	NPC44558
0.8443	Intermediate Similarity	NPC105511
0.8443	Intermediate Similarity	NPC471416
0.8443	Intermediate Similarity	NPC183357
0.8438	Intermediate Similarity	NPC244371
0.8438	Intermediate Similarity	NPC159922
0.8434	Intermediate Similarity	NPC93099
0.8434	Intermediate Similarity	NPC146792
0.8434	Intermediate Similarity	NPC135345
0.8434	Intermediate Similarity	NPC45618
0.8434	Intermediate Similarity	NPC58716
0.8431	Intermediate Similarity	NPC58137
0.8431	Intermediate Similarity	NPC300798
0.8424	Intermediate Similarity	NPC475738
0.8424	Intermediate Similarity	NPC326520
0.8424	Intermediate Similarity	NPC300053
0.8424	Intermediate Similarity	NPC222531
0.8424	Intermediate Similarity	NPC165720
0.8421	Intermediate Similarity	NPC170203
0.8418	Intermediate Similarity	NPC238140
0.8412	Intermediate Similarity	NPC241196
0.8405	Intermediate Similarity	NPC476337
0.8405	Intermediate Similarity	NPC119910
0.8402	Intermediate Similarity	NPC290304
0.8402	Intermediate Similarity	NPC236327
0.8397	Intermediate Similarity	NPC472560
0.8395	Intermediate Similarity	NPC156057
0.8395	Intermediate Similarity	NPC472910
0.8395	Intermediate Similarity	NPC48208
0.8395	Intermediate Similarity	NPC96167
0.8395	Intermediate Similarity	NPC475267
0.8395	Intermediate Similarity	NPC181960
0.8395	Intermediate Similarity	NPC245758
0.8395	Intermediate Similarity	NPC474836
0.8395	Intermediate Similarity	NPC474208
0.8395	Intermediate Similarity	NPC472911
0.8395	Intermediate Similarity	NPC19947
0.8395	Intermediate Similarity	NPC207584
0.8395	Intermediate Similarity	NPC162869
0.8395	Intermediate Similarity	NPC472914
0.8395	Intermediate Similarity	NPC222814
0.8395	Intermediate Similarity	NPC210084
0.8395	Intermediate Similarity	NPC99597
0.8395	Intermediate Similarity	NPC472913
0.8393	Intermediate Similarity	NPC48773
0.8393	Intermediate Similarity	NPC472386
0.8393	Intermediate Similarity	NPC261254
0.8393	Intermediate Similarity	NPC267254
0.8393	Intermediate Similarity	NPC235575
0.8393	Intermediate Similarity	NPC205076
0.8393	Intermediate Similarity	NPC307518
0.8387	Intermediate Similarity	NPC15743
0.8385	Intermediate Similarity	NPC472909
0.8385	Intermediate Similarity	NPC37392
0.8385	Intermediate Similarity	NPC267242
0.8383	Intermediate Similarity	NPC210042
0.8383	Intermediate Similarity	NPC201292
0.8383	Intermediate Similarity	NPC95855
0.8383	Intermediate Similarity	NPC58053
0.8383	Intermediate Similarity	NPC226294
0.8383	Intermediate Similarity	NPC186807
0.8383	Intermediate Similarity	NPC45638
0.8383	Intermediate Similarity	NPC93337
0.8383	Intermediate Similarity	NPC152477
0.8383	Intermediate Similarity	NPC183036
0.8383	Intermediate Similarity	NPC475942
0.8383	Intermediate Similarity	NPC105025
0.8383	Intermediate Similarity	NPC469931
0.8383	Intermediate Similarity	NPC211309
0.8377	Intermediate Similarity	NPC174522
0.8377	Intermediate Similarity	NPC80326
0.8375	Intermediate Similarity	NPC292460
0.8373	Intermediate Similarity	NPC128293
0.8373	Intermediate Similarity	NPC119589
0.8365	Intermediate Similarity	NPC32079
0.8365	Intermediate Similarity	NPC477700
0.8364	Intermediate Similarity	NPC88043
0.8354	Intermediate Similarity	NPC477695
0.8354	Intermediate Similarity	NPC474965
0.8354	Intermediate Similarity	NPC145569
0.8354	Intermediate Similarity	NPC668
0.8354	Intermediate Similarity	NPC115624
0.8354	Intermediate Similarity	NPC293757
0.8354	Intermediate Similarity	NPC174512
0.8354	Intermediate Similarity	NPC216223
0.8353	Intermediate Similarity	NPC473713
0.8353	Intermediate Similarity	NPC23593
0.8353	Intermediate Similarity	NPC263955
0.8344	Intermediate Similarity	NPC152904
0.8344	Intermediate Similarity	NPC476242
0.8344	Intermediate Similarity	NPC25496
0.8343	Intermediate Similarity	NPC51774
0.8343	Intermediate Similarity	NPC239549
0.8343	Intermediate Similarity	NPC236191
0.8333	Intermediate Similarity	NPC282987
0.8333	Intermediate Similarity	NPC237946
0.8333	Intermediate Similarity	NPC52353
0.8333	Intermediate Similarity	NPC475360
0.8333	Intermediate Similarity	NPC155063
0.8333	Intermediate Similarity	NPC474434
0.8333	Intermediate Similarity	NPC293004
0.8333	Intermediate Similarity	NPC303255
0.8333	Intermediate Similarity	NPC72249
0.8333	Intermediate Similarity	NPC317383
0.8333	Intermediate Similarity	NPC84265
0.8333	Intermediate Similarity	NPC32373
0.8333	Intermediate Similarity	NPC245014
0.8333	Intermediate Similarity	NPC232883
0.8323	Intermediate Similarity	NPC474948
0.8323	Intermediate Similarity	NPC45400
0.8323	Intermediate Similarity	NPC76482
0.8323	Intermediate Similarity	NPC60084
0.8323	Intermediate Similarity	NPC136757
0.8323	Intermediate Similarity	NPC42230
0.8323	Intermediate Similarity	NPC273578
0.8314	Intermediate Similarity	NPC6709
0.8313	Intermediate Similarity	NPC224280
0.8313	Intermediate Similarity	NPC477699
0.8313	Intermediate Similarity	NPC288316
0.8313	Intermediate Similarity	NPC475076
0.8313	Intermediate Similarity	NPC56184
0.8313	Intermediate Similarity	NPC204515
0.8313	Intermediate Similarity	NPC234052
0.8313	Intermediate Similarity	NPC117579
0.8303	Intermediate Similarity	NPC81679
0.8303	Intermediate Similarity	NPC215612
0.8303	Intermediate Similarity	NPC300537
0.8303	Intermediate Similarity	NPC127782
0.8303	Intermediate Similarity	NPC148273
0.8303	Intermediate Similarity	NPC76687
0.8303	Intermediate Similarity	NPC476244

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 NPC220462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	877
0.2-0.3	1927
0.3-0.4	2599
0.4-0.5	1851
0.5-0.6	931
0.6-0.7	488
0.7-0.8	109
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8434	Intermediate Similarity	NPD3818	Discontinued
0.8344	Intermediate Similarity	NPD6234	Discontinued
0.8333	Intermediate Similarity	NPD4966	Approved
0.8333	Intermediate Similarity	NPD4965	Approved
0.8333	Intermediate Similarity	NPD4967	Phase 2
0.8261	Intermediate Similarity	NPD1934	Approved
0.8242	Intermediate Similarity	NPD7199	Phase 2
0.8187	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5494	Approved
0.8148	Intermediate Similarity	NPD37	Approved
0.8144	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7074	Phase 3
0.811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7228	Approved
0.8098	Intermediate Similarity	NPD2801	Approved
0.8059	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD1653	Approved
0.8012	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD3751	Discontinued
0.7988	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3882	Suspended
0.7875	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7808	Phase 3
0.7861	Intermediate Similarity	NPD6797	Phase 2
0.7849	Intermediate Similarity	NPD5844	Phase 1
0.7816	Intermediate Similarity	NPD7240	Approved
0.7816	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD1465	Phase 2
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7764	Intermediate Similarity	NPD1511	Approved
0.773	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3817	Phase 2
0.7677	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1613	Approved
0.7669	Intermediate Similarity	NPD1512	Approved
0.7657	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6559	Discontinued
0.761	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1549	Phase 2
0.7547	Intermediate Similarity	NPD6100	Approved
0.7547	Intermediate Similarity	NPD6099	Approved
0.7543	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7456	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7473	Discontinued
0.7427	Intermediate Similarity	NPD7075	Discontinued
0.7416	Intermediate Similarity	NPD7685	Pre-registration
0.7412	Intermediate Similarity	NPD5402	Approved
0.7407	Intermediate Similarity	NPD2800	Approved
0.7405	Intermediate Similarity	NPD230	Phase 1
0.7389	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7028	Phase 2
0.7362	Intermediate Similarity	NPD3750	Approved
0.7356	Intermediate Similarity	NPD6232	Discontinued
0.7353	Intermediate Similarity	NPD7819	Suspended
0.7346	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3749	Approved
0.7325	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6190	Approved
0.731	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6674	Discontinued
0.7289	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2534	Approved
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2532	Approved
0.7289	Intermediate Similarity	NPD2533	Approved
0.7287	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.7261	Intermediate Similarity	NPD3027	Phase 3
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7243	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6799	Approved
0.7228	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2796	Approved
0.7216	Intermediate Similarity	NPD3926	Phase 2
0.7208	Intermediate Similarity	NPD4749	Approved
0.72	Intermediate Similarity	NPD6959	Discontinued
0.7193	Intermediate Similarity	NPD6801	Discontinued
0.719	Intermediate Similarity	NPD1610	Phase 2
0.719	Intermediate Similarity	NPD1091	Approved
0.719	Intermediate Similarity	NPD3705	Approved
0.7176	Intermediate Similarity	NPD6599	Discontinued
0.716	Intermediate Similarity	NPD3748	Approved
0.7159	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7151	Intermediate Similarity	NPD8455	Phase 2
0.7135	Intermediate Similarity	NPD7680	Approved
0.7135	Intermediate Similarity	NPD7411	Suspended
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.712	Intermediate Similarity	NPD8434	Phase 2
0.711	Intermediate Similarity	NPD5353	Approved
0.7107	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4908	Phase 1
0.7088	Intermediate Similarity	NPD7549	Discontinued
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD447	Suspended
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7049	Intermediate Similarity	NPD8312	Approved
0.7049	Intermediate Similarity	NPD8313	Approved
0.7048	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4110	Phase 3
0.7035	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1240	Approved
0.7019	Intermediate Similarity	NPD943	Approved
0.7006	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD920	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3268	Approved
0.6989	Remote Similarity	NPD6842	Approved
0.6989	Remote Similarity	NPD6841	Approved
0.6989	Remote Similarity	NPD6843	Phase 3
0.6988	Remote Similarity	NPD1652	Phase 2
0.6988	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2403	Approved
0.6982	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5401	Approved
0.6982	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6778	Approved
0.6979	Remote Similarity	NPD6779	Approved
0.6979	Remote Similarity	NPD6776	Approved
0.6979	Remote Similarity	NPD6780	Approved
0.6979	Remote Similarity	NPD6782	Approved
0.6979	Remote Similarity	NPD6781	Approved
0.6979	Remote Similarity	NPD6777	Approved
0.6975	Remote Similarity	NPD1933	Approved
0.697	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7266	Discontinued
0.697	Remote Similarity	NPD6004	Phase 3
0.697	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6002	Phase 3
0.697	Remote Similarity	NPD6005	Phase 3
0.6957	Remote Similarity	NPD6233	Phase 2
0.6951	Remote Similarity	NPD7033	Discontinued
0.6933	Remote Similarity	NPD1607	Approved
0.6923	Remote Similarity	NPD1608	Approved
0.6919	Remote Similarity	NPD7458	Discontinued
0.6918	Remote Similarity	NPD9494	Approved
0.6907	Remote Similarity	NPD5005	Approved
0.6907	Remote Similarity	NPD5006	Approved
0.6899	Remote Similarity	NPD2797	Approved
0.6894	Remote Similarity	NPD6798	Discontinued
0.689	Remote Similarity	NPD7097	Phase 1
0.6889	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1243	Approved
0.6872	Remote Similarity	NPD4004	Approved
0.6872	Remote Similarity	NPD5710	Approved
0.6872	Remote Similarity	NPD4002	Approved
0.6872	Remote Similarity	NPD7435	Discontinued
0.6872	Remote Similarity	NPD5711	Approved
0.6864	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD422	Phase 1
0.6856	Remote Similarity	NPD2494	Approved
0.6856	Remote Similarity	NPD2493	Approved
0.6856	Remote Similarity	NPD3452	Approved
0.6856	Remote Similarity	NPD3450	Approved
0.6848	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4583	Approved
0.6837	Remote Similarity	NPD4582	Approved
0.6833	Remote Similarity	NPD5242	Approved
0.6823	Remote Similarity	NPD2974	Approved
0.6823	Remote Similarity	NPD2975	Approved
0.6823	Remote Similarity	NPD2973	Approved
0.6818	Remote Similarity	NPD1548	Phase 1
0.6815	Remote Similarity	NPD9269	Phase 2
0.6807	Remote Similarity	NPD1551	Phase 2
0.6807	Remote Similarity	NPD2935	Discontinued
0.6804	Remote Similarity	NPD4580	Approved
0.68	Remote Similarity	NPD7783	Phase 2
0.68	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3267	Approved
0.6792	Remote Similarity	NPD3266	Approved
0.679	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1296	Phase 2
0.6789	Remote Similarity	NPD7296	Approved
0.6788	Remote Similarity	NPD4420	Approved
0.6786	Remote Similarity	NPD7696	Phase 3
0.6786	Remote Similarity	NPD7698	Approved
0.6786	Remote Similarity	NPD7697	Approved
0.6784	Remote Similarity	NPD8151	Discontinued
0.678	Remote Similarity	NPD7768	Phase 2
0.6774	Remote Similarity	NPD9268	Approved
0.6774	Remote Similarity	NPD1357	Approved
0.6772	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2344	Approved
0.6765	Remote Similarity	NPD5058	Phase 3
0.6751	Remote Similarity	NPD7871	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data