NPASS Compound

Structure

NPC115808 OpenBabel07101719512D 30 32 0 0 0 0 0 0 0 0999 V2000 3.0661 1.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7062 2.1581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2957 1.2935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2479 2.4227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3746 0.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2957 0.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2044 2.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0661 -0.2298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7118 2.3076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7062 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2981 1.9777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2479 -0.8823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5405 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1448 1.1838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0756 0.2248 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 -0.1560 1.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3411 0.6876 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5482 0.1438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1560 0.5056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3385 0.6157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2561 -0.8126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 23 2 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 20 25 1 0 0 0 0 21 27 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 25 2 0 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.26
Volume:	451.925
LogP:	8.502
LogD:	4.7
LogS:	-3.358
# Rotatable Bonds:	0
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	3.642
Fsp3:	0.538
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:	-5.356
MDCK Permeability:	1.332782267127186e-05
Pgp-inhibitor:	0.098
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	100.27377319335938%
Volume Distribution (VD):	2.812
Pgp-substrate:	0.326299786567688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.729
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.88
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.871
CYP2D6-substrate:	0.715
CYP3A4-inhibitor:	0.178
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	5.082
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.593
AMES Toxicity:	0.696
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.962
Carcinogencity:	0.022
Eye Corrosion:	0.006
Eye Irritation:	0.949
Respiratory Toxicity:	0.635

Download Data

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

Natural Product: NPC115808

Natural Product ID:	NPC115808
*Common Name:**	HKKBXNLYXSFUFL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	1,1',3,3'-Tetrahydroxyturriane
Standard InCHIKey:	HKKBXNLYXSFUFL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H36O4/c27-21-17-20-14-12-10-8-6-4-2-1-3-5-7-9-11-13-19-15-22(28)26(23(29)16-19)25(20)24(30)18-21/h15-18,27-30H,1-14H2
SMILES:	Oc1cc2CCCCCCCCCCCCCCc3cc(c(c2c(c1)O)c(O)c3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL374437
PubChem CID:	44419740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	28600.0	nM	PMID[456282]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	22800.0	nM	PMID[456282]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	27700.0	nM	PMID[456282]

☑ 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 NPC115808 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	381
0.1-0.2	1760
0.2-0.3	4894
0.3-0.4	13503
0.4-0.5	5458
0.5-0.6	6332
0.6-0.7	7598
0.7-0.8	2381
0.8-0.85	280
0.85-0.9	82
0.9-0.95	26
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC470760
0.9304	High Similarity	NPC39029
0.9273	High Similarity	NPC166995
0.9189	High Similarity	NPC263753
0.9189	High Similarity	NPC23804
0.9174	High Similarity	NPC202647
0.9107	High Similarity	NPC107240
0.9076	High Similarity	NPC82299
0.9018	High Similarity	NPC117846
0.9018	High Similarity	NPC261343
0.9009	High Similarity	NPC224527
0.9	High Similarity	NPC19808
0.9	High Similarity	NPC473221
0.9	High Similarity	NPC33728
0.8981	High Similarity	NPC246056
0.8957	High Similarity	NPC9592
0.8957	High Similarity	NPC48781
0.8929	High Similarity	NPC43525
0.8919	High Similarity	NPC224870
0.8909	High Similarity	NPC174981
0.8908	High Similarity	NPC224342
0.8899	High Similarity	NPC470700
0.8899	High Similarity	NPC109691
0.8899	High Similarity	NPC99836
0.8899	High Similarity	NPC201662
0.8899	High Similarity	NPC118286
0.8899	High Similarity	NPC302681
0.8899	High Similarity	NPC12640
0.8899	High Similarity	NPC39097
0.8899	High Similarity	NPC39664
0.8879	High Similarity	NPC217174
0.886	High Similarity	NPC246760
0.886	High Similarity	NPC84999
0.8839	High Similarity	NPC4493
0.8839	High Similarity	NPC151537
0.8839	High Similarity	NPC476632
0.8839	High Similarity	NPC165770
0.8839	High Similarity	NPC225679
0.8829	High Similarity	NPC299568
0.8829	High Similarity	NPC186385
0.8818	High Similarity	NPC232523
0.8818	High Similarity	NPC54844
0.8818	High Similarity	NPC204901
0.8818	High Similarity	NPC158253
0.8814	High Similarity	NPC237667
0.8807	High Similarity	NPC134829
0.8807	High Similarity	NPC37802
0.8807	High Similarity	NPC474839
0.8807	High Similarity	NPC292452
0.8803	High Similarity	NPC69006
0.8793	High Similarity	NPC144343
0.8793	High Similarity	NPC206
0.8729	High Similarity	NPC24125
0.8727	High Similarity	NPC248904
0.8718	High Similarity	NPC191866
0.8718	High Similarity	NPC151197
0.8716	High Similarity	NPC227458
0.8716	High Similarity	NPC102216
0.8716	High Similarity	NPC244513
0.8716	High Similarity	NPC218879
0.8716	High Similarity	NPC30506
0.8716	High Similarity	NPC119860
0.8716	High Similarity	NPC241891
0.8696	High Similarity	NPC472893
0.8667	High Similarity	NPC53567
0.8644	High Similarity	NPC472071
0.8624	High Similarity	NPC168393
0.8609	High Similarity	NPC249270
0.8596	High Similarity	NPC473521
0.8596	High Similarity	NPC46940
0.8584	High Similarity	NPC475018
0.8583	High Similarity	NPC120172
0.8571	High Similarity	NPC61885
0.8571	High Similarity	NPC63698
0.8559	High Similarity	NPC67250
0.8547	High Similarity	NPC299180
0.8547	High Similarity	NPC277588
0.8532	High Similarity	NPC192032
0.8532	High Similarity	NPC143659
0.8532	High Similarity	NPC24407
0.8532	High Similarity	NPC72947
0.8532	High Similarity	NPC137415
0.8532	High Similarity	NPC284011
0.8532	High Similarity	NPC294186
0.8532	High Similarity	NPC166313
0.8532	High Similarity	NPC11280
0.8532	High Similarity	NPC100340
0.8532	High Similarity	NPC147310
0.8525	High Similarity	NPC105031
0.8522	High Similarity	NPC319803
0.8509	High Similarity	NPC95716
0.8496	Intermediate Similarity	NPC58865
0.8487	Intermediate Similarity	NPC223451
0.8482	Intermediate Similarity	NPC151477
0.8462	Intermediate Similarity	NPC261973
0.8455	Intermediate Similarity	NPC313030
0.8455	Intermediate Similarity	NPC106396
0.8455	Intermediate Similarity	NPC71002
0.8455	Intermediate Similarity	NPC145659
0.8455	Intermediate Similarity	NPC170485
0.8455	Intermediate Similarity	NPC242342
0.8455	Intermediate Similarity	NPC302219
0.8455	Intermediate Similarity	NPC222522
0.8455	Intermediate Similarity	NPC85479
0.8455	Intermediate Similarity	NPC146798
0.8455	Intermediate Similarity	NPC53051
0.8455	Intermediate Similarity	NPC168303
0.8455	Intermediate Similarity	NPC249828
0.8455	Intermediate Similarity	NPC9292
0.8455	Intermediate Similarity	NPC94351
0.8455	Intermediate Similarity	NPC24404
0.8443	Intermediate Similarity	NPC174729
0.8443	Intermediate Similarity	NPC97578
0.8443	Intermediate Similarity	NPC139774
0.844	Intermediate Similarity	NPC10588
0.844	Intermediate Similarity	NPC248573
0.844	Intermediate Similarity	NPC161571
0.844	Intermediate Similarity	NPC275053
0.843	Intermediate Similarity	NPC122175
0.8417	Intermediate Similarity	NPC102639
0.8413	Intermediate Similarity	NPC8899
0.8413	Intermediate Similarity	NPC160623
0.8407	Intermediate Similarity	NPC95344
0.8378	Intermediate Similarity	NPC288411
0.8374	Intermediate Similarity	NPC105718
0.8374	Intermediate Similarity	NPC278955
0.8374	Intermediate Similarity	NPC113495
0.8362	Intermediate Similarity	NPC715
0.8348	Intermediate Similarity	NPC469912
0.8348	Intermediate Similarity	NPC268032
0.8346	Intermediate Similarity	NPC469611
0.8333	Intermediate Similarity	NPC314187
0.832	Intermediate Similarity	NPC215300
0.832	Intermediate Similarity	NPC38017
0.832	Intermediate Similarity	NPC148366
0.832	Intermediate Similarity	NPC311293
0.8319	Intermediate Similarity	NPC190514
0.8306	Intermediate Similarity	NPC111723
0.8306	Intermediate Similarity	NPC237517
0.8306	Intermediate Similarity	NPC91204
0.8304	Intermediate Similarity	NPC117115
0.8304	Intermediate Similarity	NPC138942
0.8293	Intermediate Similarity	NPC228503
0.8293	Intermediate Similarity	NPC138248
0.8291	Intermediate Similarity	NPC195922
0.8291	Intermediate Similarity	NPC473137
0.8288	Intermediate Similarity	NPC168829
0.8288	Intermediate Similarity	NPC233827
0.8281	Intermediate Similarity	NPC469610
0.8279	Intermediate Similarity	NPC77789
0.8279	Intermediate Similarity	NPC18128
0.8273	Intermediate Similarity	NPC166761
0.8268	Intermediate Similarity	NPC282508
0.8261	Intermediate Similarity	NPC132720
0.8261	Intermediate Similarity	NPC296683
0.8257	Intermediate Similarity	NPC32674
0.8257	Intermediate Similarity	NPC156313
0.8257	Intermediate Similarity	NPC291789
0.825	Intermediate Similarity	NPC469644
0.825	Intermediate Similarity	NPC184302
0.8246	Intermediate Similarity	NPC11554
0.824	Intermediate Similarity	NPC53781
0.824	Intermediate Similarity	NPC32715
0.824	Intermediate Similarity	NPC46978
0.824	Intermediate Similarity	NPC66331
0.824	Intermediate Similarity	NPC257947
0.824	Intermediate Similarity	NPC98200
0.8235	Intermediate Similarity	NPC304510
0.8235	Intermediate Similarity	NPC172219
0.8231	Intermediate Similarity	NPC472648
0.8231	Intermediate Similarity	NPC472649
0.8231	Intermediate Similarity	NPC191462
0.8231	Intermediate Similarity	NPC206525
0.8231	Intermediate Similarity	NPC170328
0.8231	Intermediate Similarity	NPC472647
0.8231	Intermediate Similarity	NPC133463
0.823	Intermediate Similarity	NPC54765
0.823	Intermediate Similarity	NPC21594
0.822	Intermediate Similarity	NPC232165
0.8214	Intermediate Similarity	NPC238696
0.8205	Intermediate Similarity	NPC322239
0.8198	Intermediate Similarity	NPC477685
0.8197	Intermediate Similarity	NPC476633
0.819	Intermediate Similarity	NPC176279
0.819	Intermediate Similarity	NPC260323
0.8189	Intermediate Similarity	NPC472369
0.8182	Intermediate Similarity	NPC475245
0.8182	Intermediate Similarity	NPC282255
0.8182	Intermediate Similarity	NPC273623
0.8182	Intermediate Similarity	NPC80027
0.8168	Intermediate Similarity	NPC266006
0.8168	Intermediate Similarity	NPC71465
0.8168	Intermediate Similarity	NPC35550
0.8168	Intermediate Similarity	NPC472646
0.8167	Intermediate Similarity	NPC471671
0.8158	Intermediate Similarity	NPC61033
0.8158	Intermediate Similarity	NPC305603
0.8154	Intermediate Similarity	NPC258780
0.8154	Intermediate Similarity	NPC37410
0.8151	Intermediate Similarity	NPC471668

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 NPC115808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	1006
0.2-0.3	1513
0.3-0.4	3045
0.4-0.5	1686
0.5-0.6	1088
0.6-0.7	397
0.7-0.8	61
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8829	High Similarity	NPD4750	Phase 3
0.844	Intermediate Similarity	NPD1242	Phase 1
0.8435	Intermediate Similarity	NPD7635	Approved
0.8364	Intermediate Similarity	NPD846	Approved
0.8364	Intermediate Similarity	NPD940	Approved
0.8158	Intermediate Similarity	NPD2342	Discontinued
0.811	Intermediate Similarity	NPD4625	Phase 3
0.8018	Intermediate Similarity	NPD3020	Approved
0.7909	Intermediate Similarity	NPD2859	Approved
0.7909	Intermediate Similarity	NPD844	Approved
0.7909	Intermediate Similarity	NPD2860	Approved
0.7863	Intermediate Similarity	NPD3022	Approved
0.7863	Intermediate Similarity	NPD3021	Approved
0.7838	Intermediate Similarity	NPD288	Approved
0.7818	Intermediate Similarity	NPD2934	Approved
0.7818	Intermediate Similarity	NPD2933	Approved
0.7778	Intermediate Similarity	NPD4749	Approved
0.7754	Intermediate Similarity	NPD7390	Discontinued
0.7734	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7615	Intermediate Similarity	NPD4908	Phase 1
0.7615	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2286	Discontinued
0.7557	Intermediate Similarity	NPD3027	Phase 3
0.7541	Intermediate Similarity	NPD497	Approved
0.7519	Intermediate Similarity	NPD3094	Phase 2
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7459	Intermediate Similarity	NPD498	Approved
0.7459	Intermediate Similarity	NPD495	Approved
0.7459	Intermediate Similarity	NPD496	Approved
0.744	Intermediate Similarity	NPD1548	Phase 1
0.744	Intermediate Similarity	NPD3091	Approved
0.7434	Intermediate Similarity	NPD1809	Phase 2
0.7419	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1613	Approved
0.7385	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6099	Approved
0.7372	Intermediate Similarity	NPD6100	Approved
0.7344	Intermediate Similarity	NPD3092	Approved
0.7344	Intermediate Similarity	NPD1201	Approved
0.7323	Intermediate Similarity	NPD2932	Approved
0.7323	Intermediate Similarity	NPD4059	Approved
0.7323	Intermediate Similarity	NPD3019	Approved
0.7308	Intermediate Similarity	NPD6696	Suspended
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.7259	Intermediate Similarity	NPD943	Approved
0.7257	Intermediate Similarity	NPD845	Approved
0.7252	Intermediate Similarity	NPD1470	Approved
0.7244	Intermediate Similarity	NPD4093	Discontinued
0.72	Intermediate Similarity	NPD6671	Approved
0.7188	Intermediate Similarity	NPD4626	Approved
0.7188	Intermediate Similarity	NPD3095	Discontinued
0.7154	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2568	Approved
0.7131	Intermediate Similarity	NPD1792	Phase 2
0.7092	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6405	Approved
0.7059	Intermediate Similarity	NPD6407	Approved
0.7054	Intermediate Similarity	NPD1751	Approved
0.705	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3750	Approved
0.7042	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD2228	Approved
0.704	Intermediate Similarity	NPD2234	Approved
0.704	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD2229	Approved
0.7034	Intermediate Similarity	NPD3028	Approved
0.7031	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4097	Suspended
0.7015	Intermediate Similarity	NPD5736	Approved
0.7015	Intermediate Similarity	NPD3018	Phase 2
0.7008	Intermediate Similarity	NPD7340	Approved
0.7007	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD111	Approved
0.6985	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1651	Approved
0.6966	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6232	Discontinued
0.6947	Remote Similarity	NPD1611	Approved
0.6947	Remote Similarity	NPD422	Phase 1
0.6944	Remote Similarity	NPD9093	Approved
0.6929	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD709	Approved
0.6923	Remote Similarity	NPD4589	Approved
0.6923	Remote Similarity	NPD3892	Phase 2
0.6923	Remote Similarity	NPD7473	Discontinued
0.6917	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1283	Approved
0.6906	Remote Similarity	NPD1607	Approved
0.6905	Remote Similarity	NPD1398	Phase 1
0.6905	Remote Similarity	NPD5283	Phase 1
0.6901	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5304	Approved
0.6899	Remote Similarity	NPD5303	Approved
0.6885	Remote Similarity	NPD1445	Approved
0.6885	Remote Similarity	NPD1444	Approved
0.6884	Remote Similarity	NPD2238	Phase 2
0.6883	Remote Similarity	NPD6959	Discontinued
0.6881	Remote Similarity	NPD9089	Approved
0.687	Remote Similarity	NPD3026	Approved
0.687	Remote Similarity	NPD3023	Approved
0.6867	Remote Similarity	NPD37	Approved
0.6866	Remote Similarity	NPD1164	Approved
0.6849	Remote Similarity	NPD2532	Approved
0.6849	Remote Similarity	NPD2534	Approved
0.6849	Remote Similarity	NPD2533	Approved
0.6846	Remote Similarity	NPD3025	Approved
0.6846	Remote Similarity	NPD5691	Approved
0.6846	Remote Similarity	NPD3024	Approved
0.6842	Remote Similarity	NPD2983	Phase 2
0.6842	Remote Similarity	NPD2982	Phase 2
0.6815	Remote Similarity	NPD2195	Approved
0.6815	Remote Similarity	NPD2194	Approved
0.6812	Remote Similarity	NPD6663	Approved
0.6809	Remote Similarity	NPD1510	Phase 2
0.68	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5156	Approved
0.6788	Remote Similarity	NPD5155	Approved
0.6769	Remote Similarity	NPD7330	Discontinued
0.6767	Remote Similarity	NPD2233	Approved
0.6767	Remote Similarity	NPD2232	Approved
0.6767	Remote Similarity	NPD2230	Approved
0.6767	Remote Similarity	NPD9269	Phase 2
0.6767	Remote Similarity	NPD2981	Phase 2
0.6765	Remote Similarity	NPD3636	Approved
0.6765	Remote Similarity	NPD3637	Approved
0.6765	Remote Similarity	NPD3635	Approved
0.6763	Remote Similarity	NPD1240	Approved
0.6763	Remote Similarity	NPD1555	Discontinued
0.6761	Remote Similarity	NPD2935	Discontinued
0.6753	Remote Similarity	NPD6234	Discontinued
0.6744	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1981	Approved
0.6742	Remote Similarity	NPD1983	Approved
0.6742	Remote Similarity	NPD1980	Approved
0.6739	Remote Similarity	NPD3764	Approved
0.6739	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7447	Phase 1
0.6735	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4965	Approved
0.6732	Remote Similarity	NPD4967	Phase 2
0.6732	Remote Similarity	NPD4966	Approved
0.6723	Remote Similarity	NPD9273	Approved
0.6718	Remote Similarity	NPD9268	Approved
0.6716	Remote Similarity	NPD1669	Approved
0.6715	Remote Similarity	NPD3595	Approved
0.6715	Remote Similarity	NPD2605	Approved
0.6715	Remote Similarity	NPD3594	Approved
0.6715	Remote Similarity	NPD2606	Approved
0.6713	Remote Similarity	NPD4726	Approved
0.6713	Remote Similarity	NPD4721	Approved
0.6713	Remote Similarity	NPD4725	Approved
0.6711	Remote Similarity	NPD7819	Suspended
0.6692	Remote Similarity	NPD1281	Approved
0.6692	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD859	Approved
0.6691	Remote Similarity	NPD4624	Approved
0.6691	Remote Similarity	NPD602	Approved
0.6691	Remote Similarity	NPD599	Approved
0.6691	Remote Similarity	NPD858	Approved
0.669	Remote Similarity	NPD3748	Approved
0.669	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD5314	Approved
0.6667	Remote Similarity	NPD5310	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5311	Approved
0.6667	Remote Similarity	NPD7041	Phase 2
0.6667	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3620	Phase 2
0.6643	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2979	Phase 3
0.6643	Remote Similarity	NPD3059	Approved
0.6643	Remote Similarity	NPD3062	Approved
0.6643	Remote Similarity	NPD3061	Approved
0.6625	Remote Similarity	NPD5844	Phase 1
0.6624	Remote Similarity	NPD7229	Phase 3
0.6622	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6674	Discontinued
0.662	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4103	Phase 2
0.6618	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD228	Approved
0.6613	Remote Similarity	NPD968	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