NPASS Compound

Structure

NPC475833 OpenBabel07101718222D 27 29 0 0 1 0 0 0 0 0999 V2000 3.4641 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 -4.5000 0.8660 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 -0.5000 -0.8660 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -2.5981 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 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 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 20 1 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 1 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 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 20 22 1 1 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 22 4 1 1 0 0 0 23 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.21
Volume:	400.037
LogP:	3.771
LogD:	3.404
LogS:	-4.806
# Rotatable Bonds:	4
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	4.351
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.628
MDCK Permeability:	2.7700933060259558e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	92.63740539550781%
Volume Distribution (VD):	1.291
Pgp-substrate:	8.046225547790527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.805
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.945
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	3.374
Half-life (T1/2):	0.322

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.508
AMES Toxicity:	0.21
Rat Oral Acute Toxicity:	0.581
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.969
Carcinogencity:	0.719
Eye Corrosion:	0.645
Eye Irritation:	0.522
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC475833

Natural Product ID:	NPC475833
*Common Name:**	6'-Acetoxyavarone
IUPAC Name:	[2-[[(1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-3,6-dioxocyclohexa-1,4-dien-1-yl] acetate
Synonyms:	6'-Acetoxyavarone
Standard InCHIKey:	LVTXQIOTYUWIRG-APQCTARYSA-N
Standard InCHI:	InChI=1S/C23H30O4/c1-14-7-6-8-20-22(14,4)12-11-15(2)23(20,5)13-17-18(25)9-10-19(26)21(17)27-16(3)24/h7,9-10,15,20H,6,8,11-13H2,1-5H3/t15-,20+,22+,23+/m0/s1
SMILES:	CC1CCC2(C(C1(C)CC3=C(C(=O)C=CC3=O)OC(=O)C)CCC=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517033
PubChem CID:	452332
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO33143	Dysidea cinerea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1710654]
NPO33143	Dysidea cinerea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31532203]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[491613]

☑ 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 NPC475833 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	215
0.1-0.2	1711
0.2-0.3	7304
0.3-0.4	15641
0.4-0.5	9418
0.5-0.6	6194
0.6-0.7	1955
0.7-0.8	247
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC99308
0.859	High Similarity	NPC1254
0.8519	High Similarity	NPC474085
0.84	Intermediate Similarity	NPC188292
0.84	Intermediate Similarity	NPC260474
0.8333	Intermediate Similarity	NPC263997
0.8333	Intermediate Similarity	NPC132228
0.8333	Intermediate Similarity	NPC8518
0.8333	Intermediate Similarity	NPC133652
0.8158	Intermediate Similarity	NPC87141
0.8118	Intermediate Similarity	NPC6185
0.8118	Intermediate Similarity	NPC241512
0.8118	Intermediate Similarity	NPC474680
0.8095	Intermediate Similarity	NPC105803
0.8072	Intermediate Similarity	NPC55869
0.8049	Intermediate Similarity	NPC27817
0.8023	Intermediate Similarity	NPC472863
0.8	Intermediate Similarity	NPC476346
0.8	Intermediate Similarity	NPC251118
0.7952	Intermediate Similarity	NPC108955
0.7931	Intermediate Similarity	NPC163016
0.7931	Intermediate Similarity	NPC75315
0.7922	Intermediate Similarity	NPC310992
0.7901	Intermediate Similarity	NPC26504
0.7882	Intermediate Similarity	NPC118423
0.7865	Intermediate Similarity	NPC223093
0.7848	Intermediate Similarity	NPC474539
0.7848	Intermediate Similarity	NPC54123
0.7821	Intermediate Similarity	NPC256846
0.7816	Intermediate Similarity	NPC168248
0.7805	Intermediate Similarity	NPC472300
0.7778	Intermediate Similarity	NPC65650
0.7765	Intermediate Similarity	NPC327969
0.7765	Intermediate Similarity	NPC268122
0.7765	Intermediate Similarity	NPC321289
0.7753	Intermediate Similarity	NPC305039
0.7753	Intermediate Similarity	NPC280833
0.775	Intermediate Similarity	NPC56747
0.775	Intermediate Similarity	NPC470044
0.775	Intermediate Similarity	NPC470045
0.775	Intermediate Similarity	NPC180015
0.775	Intermediate Similarity	NPC130016
0.775	Intermediate Similarity	NPC109576
0.7733	Intermediate Similarity	NPC288253
0.7722	Intermediate Similarity	NPC251929
0.7722	Intermediate Similarity	NPC265782
0.7722	Intermediate Similarity	NPC2634
0.7711	Intermediate Similarity	NPC74410
0.7701	Intermediate Similarity	NPC90287
0.7692	Intermediate Similarity	NPC263780
0.7683	Intermediate Similarity	NPC180886
0.7683	Intermediate Similarity	NPC474463
0.7683	Intermediate Similarity	NPC110725
0.7654	Intermediate Similarity	NPC20025
0.7654	Intermediate Similarity	NPC147438
0.7647	Intermediate Similarity	NPC225515
0.7647	Intermediate Similarity	NPC470034
0.7647	Intermediate Similarity	NPC278459
0.7647	Intermediate Similarity	NPC475863
0.7632	Intermediate Similarity	NPC469662
0.7619	Intermediate Similarity	NPC192329
0.7595	Intermediate Similarity	NPC139397
0.7586	Intermediate Similarity	NPC320801
0.7582	Intermediate Similarity	NPC470036
0.7582	Intermediate Similarity	NPC174167
0.7579	Intermediate Similarity	NPC104861
0.7558	Intermediate Similarity	NPC142253
0.7558	Intermediate Similarity	NPC94200
0.7558	Intermediate Similarity	NPC3511
0.7558	Intermediate Similarity	NPC103486
0.7556	Intermediate Similarity	NPC112454
0.7556	Intermediate Similarity	NPC474844
0.7531	Intermediate Similarity	NPC303613
0.7531	Intermediate Similarity	NPC474228
0.7531	Intermediate Similarity	NPC251705
0.7529	Intermediate Similarity	NPC287063
0.7529	Intermediate Similarity	NPC26139
0.7528	Intermediate Similarity	NPC30421
0.7527	Intermediate Similarity	NPC147232
0.7527	Intermediate Similarity	NPC295347
0.7526	Intermediate Similarity	NPC179208
0.75	Intermediate Similarity	NPC202118
0.75	Intermediate Similarity	NPC2709
0.75	Intermediate Similarity	NPC307176
0.75	Intermediate Similarity	NPC197238
0.75	Intermediate Similarity	NPC189311
0.75	Intermediate Similarity	NPC30321
0.75	Intermediate Similarity	NPC474537
0.75	Intermediate Similarity	NPC8571
0.75	Intermediate Similarity	NPC189485
0.75	Intermediate Similarity	NPC260040
0.7473	Intermediate Similarity	NPC474209
0.7473	Intermediate Similarity	NPC475823
0.7471	Intermediate Similarity	NPC470015
0.7471	Intermediate Similarity	NPC474790
0.7471	Intermediate Similarity	NPC49019
0.7471	Intermediate Similarity	NPC168188
0.7471	Intermediate Similarity	NPC474976
0.747	Intermediate Similarity	NPC92080
0.747	Intermediate Similarity	NPC69408
0.747	Intermediate Similarity	NPC40353
0.7468	Intermediate Similarity	NPC155198
0.7467	Intermediate Similarity	NPC127582
0.7444	Intermediate Similarity	NPC472302
0.7444	Intermediate Similarity	NPC196407
0.7439	Intermediate Similarity	NPC329866
0.7439	Intermediate Similarity	NPC309852
0.7439	Intermediate Similarity	NPC474796
0.7439	Intermediate Similarity	NPC474797
0.7423	Intermediate Similarity	NPC308351
0.7423	Intermediate Similarity	NPC271266
0.7416	Intermediate Similarity	NPC220478
0.7407	Intermediate Similarity	NPC305501
0.7407	Intermediate Similarity	NPC133253
0.7407	Intermediate Similarity	NPC21944
0.7407	Intermediate Similarity	NPC190035
0.7407	Intermediate Similarity	NPC115023
0.7407	Intermediate Similarity	NPC5701
0.7407	Intermediate Similarity	NPC225467
0.7407	Intermediate Similarity	NPC234707
0.7403	Intermediate Similarity	NPC475124
0.7403	Intermediate Similarity	NPC285371
0.7386	Intermediate Similarity	NPC474359
0.7386	Intermediate Similarity	NPC87552
0.7381	Intermediate Similarity	NPC165711
0.7381	Intermediate Similarity	NPC283087
0.7368	Intermediate Similarity	NPC208094
0.7363	Intermediate Similarity	NPC284561
0.7356	Intermediate Similarity	NPC100297
0.7356	Intermediate Similarity	NPC472239
0.7356	Intermediate Similarity	NPC469806
0.7356	Intermediate Similarity	NPC302661
0.7356	Intermediate Similarity	NPC469804
0.7356	Intermediate Similarity	NPC238991
0.7356	Intermediate Similarity	NPC469805
0.7356	Intermediate Similarity	NPC469799
0.7356	Intermediate Similarity	NPC472867
0.7349	Intermediate Similarity	NPC293803
0.7349	Intermediate Similarity	NPC473171
0.734	Intermediate Similarity	NPC171395
0.734	Intermediate Similarity	NPC777
0.7333	Intermediate Similarity	NPC276764
0.7333	Intermediate Similarity	NPC472304
0.7333	Intermediate Similarity	NPC181327
0.7326	Intermediate Similarity	NPC474956
0.7326	Intermediate Similarity	NPC469798
0.7326	Intermediate Similarity	NPC469797
0.7312	Intermediate Similarity	NPC469939
0.7312	Intermediate Similarity	NPC271652
0.7312	Intermediate Similarity	NPC79117
0.7303	Intermediate Similarity	NPC94531
0.7303	Intermediate Similarity	NPC323765
0.7303	Intermediate Similarity	NPC123319
0.7303	Intermediate Similarity	NPC33881
0.7303	Intermediate Similarity	NPC29447
0.7303	Intermediate Similarity	NPC11711
0.7303	Intermediate Similarity	NPC311702
0.7303	Intermediate Similarity	NPC33663
0.7303	Intermediate Similarity	NPC255174
0.7294	Intermediate Similarity	NPC4827
0.7294	Intermediate Similarity	NPC469996
0.7294	Intermediate Similarity	NPC23778
0.7284	Intermediate Similarity	NPC35734
0.7284	Intermediate Similarity	NPC159577
0.7284	Intermediate Similarity	NPC282593
0.7273	Intermediate Similarity	NPC53733
0.7273	Intermediate Similarity	NPC3856
0.7273	Intermediate Similarity	NPC279639
0.7273	Intermediate Similarity	NPC288281
0.7262	Intermediate Similarity	NPC19907
0.7262	Intermediate Similarity	NPC69143
0.7262	Intermediate Similarity	NPC899
0.7253	Intermediate Similarity	NPC72397
0.7253	Intermediate Similarity	NPC215831
0.725	Intermediate Similarity	NPC134385
0.7241	Intermediate Similarity	NPC474955
0.7241	Intermediate Similarity	NPC471898
0.7241	Intermediate Similarity	NPC116797
0.7241	Intermediate Similarity	NPC474353
0.7241	Intermediate Similarity	NPC149237
0.7229	Intermediate Similarity	NPC219232
0.7229	Intermediate Similarity	NPC241854
0.7229	Intermediate Similarity	NPC255021
0.7229	Intermediate Similarity	NPC476046
0.7229	Intermediate Similarity	NPC251970
0.7229	Intermediate Similarity	NPC166797
0.7229	Intermediate Similarity	NPC128346
0.7222	Intermediate Similarity	NPC195640
0.7216	Intermediate Similarity	NPC472972
0.7215	Intermediate Similarity	NPC323005
0.7209	Intermediate Similarity	NPC190211
0.7209	Intermediate Similarity	NPC476177
0.7209	Intermediate Similarity	NPC90965
0.7209	Intermediate Similarity	NPC170793
0.7209	Intermediate Similarity	NPC475681
0.7204	Intermediate Similarity	NPC204341
0.7204	Intermediate Similarity	NPC218301
0.72	Intermediate Similarity	NPC27610
0.72	Intermediate Similarity	NPC311852
0.72	Intermediate Similarity	NPC470267

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 NPC475833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1834
0.2-0.3	4261
0.3-0.4	2007
0.4-0.5	543
0.5-0.6	160
0.6-0.7	115
0.7-0.8	22
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
0.7978	Intermediate Similarity	NPD5694	Approved
0.7865	Intermediate Similarity	NPD5692	Phase 3
0.7841	Intermediate Similarity	NPD6672	Approved
0.7841	Intermediate Similarity	NPD5737	Approved
0.7778	Intermediate Similarity	NPD6050	Approved
0.7753	Intermediate Similarity	NPD6673	Approved
0.7753	Intermediate Similarity	NPD6080	Approved
0.7753	Intermediate Similarity	NPD6904	Approved
0.7738	Intermediate Similarity	NPD4695	Discontinued
0.7722	Intermediate Similarity	NPD4691	Approved
0.7654	Intermediate Similarity	NPD4058	Approved
0.7654	Intermediate Similarity	NPD4687	Approved
0.7595	Intermediate Similarity	NPD4137	Phase 3
0.7582	Intermediate Similarity	NPD5693	Phase 1
0.7556	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD3573	Approved
0.7527	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD4747	Approved
0.7439	Intermediate Similarity	NPD5733	Approved
0.7416	Intermediate Similarity	NPD6098	Approved
0.7407	Intermediate Similarity	NPD5276	Approved
0.734	Intermediate Similarity	NPD5654	Approved
0.7283	Intermediate Similarity	NPD5207	Approved
0.7222	Intermediate Similarity	NPD5690	Phase 2
0.7222	Intermediate Similarity	NPD7146	Approved
0.7222	Intermediate Similarity	NPD7334	Approved
0.7222	Intermediate Similarity	NPD7521	Approved
0.7222	Intermediate Similarity	NPD5330	Approved
0.7222	Intermediate Similarity	NPD6409	Approved
0.7222	Intermediate Similarity	NPD6684	Approved
0.7188	Intermediate Similarity	NPD6083	Phase 2
0.7188	Intermediate Similarity	NPD5959	Approved
0.7188	Intermediate Similarity	NPD6084	Phase 2
0.7113	Intermediate Similarity	NPD5696	Approved
0.7079	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6903	Approved
0.7065	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5208	Approved
0.7037	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5281	Approved
0.7021	Intermediate Similarity	NPD5284	Approved
0.6966	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6614	Approved
0.6961	Remote Similarity	NPD5697	Approved
0.6897	Remote Similarity	NPD3617	Approved
0.6893	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD6899	Approved
0.6893	Remote Similarity	NPD6011	Approved
0.6875	Remote Similarity	NPD7900	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.6875	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8028	Phase 2
0.6848	Remote Similarity	NPD4694	Approved
0.6848	Remote Similarity	NPD5280	Approved
0.6827	Remote Similarity	NPD6012	Approved
0.6827	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD6014	Approved
0.6813	Remote Similarity	NPD4197	Approved
0.6804	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6399	Phase 3
0.6762	Remote Similarity	NPD7290	Approved
0.6762	Remote Similarity	NPD6883	Approved
0.6762	Remote Similarity	NPD7102	Approved
0.6753	Remote Similarity	NPD287	Approved
0.6739	Remote Similarity	NPD5329	Approved
0.6739	Remote Similarity	NPD1694	Approved
0.6735	Remote Similarity	NPD7732	Phase 3
0.6701	Remote Similarity	NPD6001	Approved
0.6699	Remote Similarity	NPD6675	Approved
0.6699	Remote Similarity	NPD7128	Approved
0.6699	Remote Similarity	NPD6402	Approved
0.6699	Remote Similarity	NPD5739	Approved
0.6698	Remote Similarity	NPD6847	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD6869	Approved
0.6698	Remote Similarity	NPD6650	Approved
0.6698	Remote Similarity	NPD6617	Approved
0.6698	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD5701	Approved
0.6633	Remote Similarity	NPD4629	Approved
0.6633	Remote Similarity	NPD5210	Approved
0.6632	Remote Similarity	NPD4753	Phase 2
0.6593	Remote Similarity	NPD4221	Approved
0.6593	Remote Similarity	NPD4223	Phase 3
0.6591	Remote Similarity	NPD4756	Discovery
0.6571	Remote Similarity	NPD7320	Approved
0.6566	Remote Similarity	NPD5222	Approved
0.6566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7614	Phase 1
0.6566	Remote Similarity	NPD5221	Approved
0.6556	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6372	Approved
0.6509	Remote Similarity	NPD6373	Approved
0.65	Remote Similarity	NPD5173	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD4519	Discontinued
0.6489	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4623	Approved
0.6455	Remote Similarity	NPD6868	Approved
0.6452	Remote Similarity	NPD3668	Phase 3
0.6452	Remote Similarity	NPD3666	Approved
0.6452	Remote Similarity	NPD3133	Approved
0.6452	Remote Similarity	NPD3665	Phase 1
0.6413	Remote Similarity	NPD3667	Approved
0.6396	Remote Similarity	NPD6317	Approved
0.6389	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6008	Approved
0.6373	Remote Similarity	NPD5285	Approved
0.6373	Remote Similarity	NPD5286	Approved
0.6373	Remote Similarity	NPD4696	Approved
0.6346	Remote Similarity	NPD6052	Approved
0.6339	Remote Similarity	NPD6313	Approved
0.6339	Remote Similarity	NPD6335	Approved
0.6339	Remote Similarity	NPD6314	Approved
0.6327	Remote Similarity	NPD6079	Approved
0.6316	Remote Similarity	NPD5205	Approved
0.6316	Remote Similarity	NPD4689	Approved
0.6316	Remote Similarity	NPD4690	Approved
0.6316	Remote Similarity	NPD4693	Phase 3
0.6316	Remote Similarity	NPD4688	Approved
0.6316	Remote Similarity	NPD4138	Approved
0.6316	Remote Similarity	NPD3618	Phase 1
0.6311	Remote Similarity	NPD5223	Approved
0.6306	Remote Similarity	NPD6274	Approved
0.6289	Remote Similarity	NPD6101	Approved
0.6289	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7101	Approved
0.6283	Remote Similarity	NPD7100	Approved
0.6277	Remote Similarity	NPD4786	Approved
0.6273	Remote Similarity	NPD4632	Approved
0.6264	Remote Similarity	NPD4195	Approved
0.6263	Remote Similarity	NPD5133	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD5091	Approved
0.6238	Remote Similarity	NPD4697	Phase 3
0.6228	Remote Similarity	NPD6319	Approved
0.622	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5282	Discontinued
0.619	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD5174	Approved
0.6186	Remote Similarity	NPD4518	Approved
0.618	Remote Similarity	NPD8039	Approved
0.6176	Remote Similarity	NPD4755	Approved
0.6174	Remote Similarity	NPD5983	Phase 2
0.6132	Remote Similarity	NPD5141	Approved
0.6122	Remote Similarity	NPD5328	Approved
0.6106	Remote Similarity	NPD7115	Discovery
0.6098	Remote Similarity	NPD4191	Approved
0.6098	Remote Similarity	NPD4192	Approved
0.6098	Remote Similarity	NPD4194	Approved
0.6098	Remote Similarity	NPD4193	Approved
0.6068	Remote Similarity	NPD7604	Phase 2
0.6064	Remote Similarity	NPD5209	Approved
0.6061	Remote Similarity	NPD4096	Approved
0.6058	Remote Similarity	NPD4700	Approved
0.6058	Remote Similarity	NPD6404	Discontinued
0.6034	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3495	Discontinued
0.6017	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD8779	Phase 3
0.6	Remote Similarity	NPD3704	Approved
0.5966	Remote Similarity	NPD6336	Discontinued
0.5966	Remote Similarity	NPD6616	Approved
0.5963	Remote Similarity	NPD4730	Approved
0.5963	Remote Similarity	NPD5168	Approved
0.5963	Remote Similarity	NPD4729	Approved
0.5962	Remote Similarity	NPD7638	Approved
0.5957	Remote Similarity	NPD4692	Approved
0.5957	Remote Similarity	NPD4139	Approved
0.5952	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6054	Approved
0.5941	Remote Similarity	NPD4202	Approved
0.5941	Remote Similarity	NPD5778	Approved
0.5941	Remote Similarity	NPD5779	Approved
0.5917	Remote Similarity	NPD7078	Approved
0.5905	Remote Similarity	NPD7639	Approved
0.5905	Remote Similarity	NPD7640	Approved
0.59	Remote Similarity	NPD5785	Approved
0.5897	Remote Similarity	NPD6016	Approved
0.5897	Remote Similarity	NPD6908	Approved
0.5897	Remote Similarity	NPD6909	Approved
0.5897	Remote Similarity	NPD6015	Approved
0.5888	Remote Similarity	NPD4754	Approved
0.5872	Remote Similarity	NPD6412	Phase 2
0.5868	Remote Similarity	NPD7736	Approved
0.5856	Remote Similarity	NPD5135	Approved
0.5856	Remote Similarity	NPD5247	Approved
0.5856	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4634	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