NPASS Compound

Structure

NPC292256 OpenBabel07101718232D 27 29 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 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 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 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 -0.8660 1.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 -1.7321 0.0000 0.0000 C 0 0 0 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 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 22 1 0 0 0 0 4 22 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 15 24 2 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 23 1 1 0 0 0 18 25 1 0 0 0 0 19 21 2 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 1 0 0 0 21 26 1 0 0 0 0 23 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.23
Volume:	402.673
LogP:	5.562
LogD:	3.879
LogS:	-3.779
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	3.95
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.7
MDCK Permeability:	2.218282679677941e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.247
Plasma Protein Binding (PPB):	98.44108581542969%
Volume Distribution (VD):	1.779
Pgp-substrate:	4.522033214569092%

ADMET: Metabolism

CYP1A2-inhibitor:	0.347
CYP1A2-substrate:	0.257
CYP2C19-inhibitor:	0.366
CYP2C19-substrate:	0.475
CYP2C9-inhibitor:	0.404
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.447
CYP2D6-substrate:	0.724
CYP3A4-inhibitor:	0.3
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	8.749
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.025
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.659
Maximum Recommended Daily Dose:	0.307
Skin Sensitization:	0.791
Carcinogencity:	0.207
Eye Corrosion:	0.088
Eye Irritation:	0.904
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC292256

Natural Product ID:	NPC292256
*Common Name:**	20-O-Acetyl-21-Hydroxy-Ent-Isozonarol
IUPAC Name:	[3-[[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]methyl]-2,4-dihydroxyphenyl] acetate
Synonyms:
Standard InCHIKey:	LISRCGYCVNHXKP-KPDCDPCYSA-N
Standard InCHI:	InChI=1S/C23H32O4/c1-14-7-10-20-22(3,4)11-6-12-23(20,5)17(14)13-16-18(25)8-9-19(21(16)26)27-15(2)24/h7-9,17,20,25-26H,6,10-13H2,1-5H3/t17-,20-,23+/m0/s1
SMILES:	CC(=O)Oc1ccc(c(c1O)C[C@H]1C(=CC[C@@H]2[C@]1(C)CCCC2(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517764
PubChem CID:	11245734
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002319] Phenol esters

*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
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921404]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593283]
NPO32992	dysidea cf. cristagalli	Species	Dysideidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[16180831]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18198840]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	at 1020 m depth from Chuuk Atoll, Federated States of Micronesia	n.a.	PMID[18824352]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20230038]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26551342]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26863083]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27336796]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32243140]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[7494145]
NPO32617	dysidea sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748373]

☑ 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
GI50	3
IC50	2
Others	6

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	370.0	nM	PMID[516320]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	10500.0	nM	PMID[516321]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	=	11000.0	nM	PMID[516321]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	=	11800.0	nM	PMID[516321]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	10500.0	nM	PMID[516321]
NPT81	Cell Line	A549	Homo sapiens	TGI	=	11000.0	nM	PMID[516321]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	11800.0	nM	PMID[516321]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	11300.0	nM	PMID[516321]
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	12600.0	nM	PMID[516321]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	14000.0	nM	PMID[516321]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[516320]

☑ 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 NPC292256 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	348
0.1-0.2	1539
0.2-0.3	3489
0.3-0.4	9015
0.4-0.5	9970
0.5-0.6	4250
0.6-0.7	8934
0.7-0.8	4762
0.8-0.85	352
0.85-0.9	35
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC475896
0.9071	High Similarity	NPC105493
0.9065	High Similarity	NPC252095
0.9058	High Similarity	NPC474810
0.9051	High Similarity	NPC147317
0.9007	High Similarity	NPC19869
0.8986	High Similarity	NPC474635
0.8951	High Similarity	NPC323126
0.8936	High Similarity	NPC474540
0.8936	High Similarity	NPC474521
0.8936	High Similarity	NPC476171
0.8936	High Similarity	NPC474530
0.8913	High Similarity	NPC142530
0.8904	High Similarity	NPC170239
0.8904	High Similarity	NPC275125
0.8904	High Similarity	NPC97937
0.8794	High Similarity	NPC327382
0.8784	High Similarity	NPC113790
0.8767	High Similarity	NPC125617
0.8759	High Similarity	NPC34245
0.8759	High Similarity	NPC256555
0.8759	High Similarity	NPC110067
0.8759	High Similarity	NPC91492
0.8759	High Similarity	NPC7439
0.871	High Similarity	NPC140346
0.8707	High Similarity	NPC475872
0.8696	High Similarity	NPC176590
0.8681	High Similarity	NPC234568
0.8681	High Similarity	NPC198038
0.8639	High Similarity	NPC90645
0.8621	High Similarity	NPC35216
0.8611	High Similarity	NPC127218
0.8611	High Similarity	NPC25966
0.8611	High Similarity	NPC245207
0.8611	High Similarity	NPC319647
0.86	High Similarity	NPC195561
0.8571	High Similarity	NPC474617
0.8571	High Similarity	NPC50250
0.8571	High Similarity	NPC220935
0.8562	High Similarity	NPC469564
0.8561	High Similarity	NPC474636
0.8552	High Similarity	NPC259519
0.8543	High Similarity	NPC2745
0.8542	High Similarity	NPC276490
0.8542	High Similarity	NPC38874
0.8531	High Similarity	NPC201357
0.8531	High Similarity	NPC255147
0.8531	High Similarity	NPC281521
0.8523	High Similarity	NPC178129
0.8514	High Similarity	NPC472457
0.8511	High Similarity	NPC232275
0.8503	High Similarity	NPC6568
0.8503	High Similarity	NPC230157
0.8503	High Similarity	NPC236419
0.8497	Intermediate Similarity	NPC7178
0.8497	Intermediate Similarity	NPC62903
0.8493	Intermediate Similarity	NPC471389
0.8489	Intermediate Similarity	NPC474670
0.8489	Intermediate Similarity	NPC474821
0.8487	Intermediate Similarity	NPC157783
0.8483	Intermediate Similarity	NPC70682
0.8483	Intermediate Similarity	NPC79622
0.8483	Intermediate Similarity	NPC29868
0.8483	Intermediate Similarity	NPC212942
0.8483	Intermediate Similarity	NPC260741
0.8477	Intermediate Similarity	NPC158784
0.8472	Intermediate Similarity	NPC173660
0.8472	Intermediate Similarity	NPC270456
0.8472	Intermediate Similarity	NPC265433
0.8472	Intermediate Similarity	NPC248727
0.8472	Intermediate Similarity	NPC162659
0.8467	Intermediate Similarity	NPC212142
0.8462	Intermediate Similarity	NPC209199
0.8456	Intermediate Similarity	NPC112251
0.8451	Intermediate Similarity	NPC6451
0.8446	Intermediate Similarity	NPC280092
0.8446	Intermediate Similarity	NPC93323
0.8446	Intermediate Similarity	NPC63879
0.8446	Intermediate Similarity	NPC12641
0.8446	Intermediate Similarity	NPC45257
0.8446	Intermediate Similarity	NPC473845
0.8442	Intermediate Similarity	NPC125709
0.8442	Intermediate Similarity	NPC142479
0.8442	Intermediate Similarity	NPC155015
0.8442	Intermediate Similarity	NPC292385
0.8435	Intermediate Similarity	NPC107161
0.8429	Intermediate Similarity	NPC474616
0.8429	Intermediate Similarity	NPC266691
0.8425	Intermediate Similarity	NPC254759
0.8425	Intermediate Similarity	NPC160283
0.8421	Intermediate Similarity	NPC302915
0.8417	Intermediate Similarity	NPC474632
0.8417	Intermediate Similarity	NPC112596
0.8414	Intermediate Similarity	NPC95162
0.8414	Intermediate Similarity	NPC52086
0.8414	Intermediate Similarity	NPC20511
0.8414	Intermediate Similarity	NPC148835
0.8414	Intermediate Similarity	NPC326797
0.8414	Intermediate Similarity	NPC107551
0.8414	Intermediate Similarity	NPC474886
0.8414	Intermediate Similarity	NPC76336
0.8414	Intermediate Similarity	NPC102904
0.8414	Intermediate Similarity	NPC176051
0.8414	Intermediate Similarity	NPC474282
0.8414	Intermediate Similarity	NPC103976
0.8414	Intermediate Similarity	NPC139548
0.8411	Intermediate Similarity	NPC30688
0.8411	Intermediate Similarity	NPC176903
0.8403	Intermediate Similarity	NPC134968
0.8403	Intermediate Similarity	NPC261873
0.8403	Intermediate Similarity	NPC313081
0.8403	Intermediate Similarity	NPC283009
0.8403	Intermediate Similarity	NPC195022
0.8392	Intermediate Similarity	NPC277021
0.8392	Intermediate Similarity	NPC37196
0.8392	Intermediate Similarity	NPC269528
0.8392	Intermediate Similarity	NPC94236
0.838	Intermediate Similarity	NPC45715
0.838	Intermediate Similarity	NPC474356
0.838	Intermediate Similarity	NPC82503
0.838	Intermediate Similarity	NPC12275
0.8378	Intermediate Similarity	NPC85264
0.8378	Intermediate Similarity	NPC102044
0.8378	Intermediate Similarity	NPC47633
0.8378	Intermediate Similarity	NPC474104
0.8378	Intermediate Similarity	NPC477616
0.8377	Intermediate Similarity	NPC268484
0.8367	Intermediate Similarity	NPC247291
0.8366	Intermediate Similarity	NPC325860
0.8366	Intermediate Similarity	NPC160196
0.8357	Intermediate Similarity	NPC50368
0.8357	Intermediate Similarity	NPC216836
0.8356	Intermediate Similarity	NPC471388
0.8356	Intermediate Similarity	NPC184613
0.8356	Intermediate Similarity	NPC132723
0.8356	Intermediate Similarity	NPC292882
0.8356	Intermediate Similarity	NPC13067
0.8356	Intermediate Similarity	NPC76032
0.8355	Intermediate Similarity	NPC21184
0.8355	Intermediate Similarity	NPC24425
0.8355	Intermediate Similarity	NPC205727
0.8355	Intermediate Similarity	NPC120426
0.8355	Intermediate Similarity	NPC294522
0.8345	Intermediate Similarity	NPC286843
0.8345	Intermediate Similarity	NPC205442
0.8345	Intermediate Similarity	NPC202846
0.8345	Intermediate Similarity	NPC472336
0.8345	Intermediate Similarity	NPC143139
0.8345	Intermediate Similarity	NPC476639
0.8345	Intermediate Similarity	NPC472334
0.8345	Intermediate Similarity	NPC82271
0.8345	Intermediate Similarity	NPC126682
0.8345	Intermediate Similarity	NPC114155
0.8345	Intermediate Similarity	NPC300846
0.8344	Intermediate Similarity	NPC473876
0.8344	Intermediate Similarity	NPC139839
0.8333	Intermediate Similarity	NPC317380
0.8333	Intermediate Similarity	NPC103967
0.8333	Intermediate Similarity	NPC474054
0.8333	Intermediate Similarity	NPC106215
0.8333	Intermediate Similarity	NPC474600
0.8322	Intermediate Similarity	NPC202762
0.8322	Intermediate Similarity	NPC161203
0.8322	Intermediate Similarity	NPC86655
0.8322	Intermediate Similarity	NPC473108
0.8322	Intermediate Similarity	NPC469795
0.8322	Intermediate Similarity	NPC87883
0.8322	Intermediate Similarity	NPC127624
0.8312	Intermediate Similarity	NPC223720
0.8312	Intermediate Similarity	NPC476154
0.8312	Intermediate Similarity	NPC149735
0.8311	Intermediate Similarity	NPC59841
0.8311	Intermediate Similarity	NPC131971
0.8311	Intermediate Similarity	NPC204347
0.8311	Intermediate Similarity	NPC175838
0.8311	Intermediate Similarity	NPC472335
0.8311	Intermediate Similarity	NPC2613
0.8311	Intermediate Similarity	NPC472332
0.8311	Intermediate Similarity	NPC475891
0.831	Intermediate Similarity	NPC299221
0.831	Intermediate Similarity	NPC224157
0.831	Intermediate Similarity	NPC311680
0.831	Intermediate Similarity	NPC234488
0.831	Intermediate Similarity	NPC214860
0.831	Intermediate Similarity	NPC51840
0.831	Intermediate Similarity	NPC192687
0.8299	Intermediate Similarity	NPC144284
0.8299	Intermediate Similarity	NPC295719
0.8299	Intermediate Similarity	NPC184797
0.8299	Intermediate Similarity	NPC27495
0.8299	Intermediate Similarity	NPC73505
0.8299	Intermediate Similarity	NPC165026
0.8299	Intermediate Similarity	NPC309124
0.8299	Intermediate Similarity	NPC34431
0.8289	Intermediate Similarity	NPC476969
0.8288	Intermediate Similarity	NPC272157
0.8288	Intermediate Similarity	NPC201145
0.8288	Intermediate Similarity	NPC35550
0.8288	Intermediate Similarity	NPC73535
0.8288	Intermediate Similarity	NPC6262

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 NPC292256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	885
0.2-0.3	1798
0.3-0.4	2779
0.4-0.5	1783
0.5-0.6	979
0.6-0.7	543
0.7-0.8	82
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
0.8188	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1613	Approved
0.7945	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4749	Approved
0.7935	Intermediate Similarity	NPD1653	Approved
0.7919	Intermediate Similarity	NPD6099	Approved
0.7919	Intermediate Similarity	NPD6100	Approved
0.7862	Intermediate Similarity	NPD4625	Phase 3
0.7862	Intermediate Similarity	NPD3027	Phase 3
0.7826	Intermediate Similarity	NPD6234	Discontinued
0.7823	Intermediate Similarity	NPD4060	Phase 1
0.7778	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.7748	Intermediate Similarity	NPD5763	Approved
0.7748	Intermediate Similarity	NPD5762	Approved
0.7688	Intermediate Similarity	NPD2801	Approved
0.7676	Intermediate Similarity	NPD1611	Approved
0.7639	Intermediate Similarity	NPD6696	Suspended
0.7625	Intermediate Similarity	NPD37	Approved
0.7619	Intermediate Similarity	NPD7095	Approved
0.7605	Intermediate Similarity	NPD7228	Approved
0.7593	Intermediate Similarity	NPD4967	Phase 2
0.7593	Intermediate Similarity	NPD4966	Approved
0.7593	Intermediate Similarity	NPD4965	Approved
0.758	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1465	Phase 2
0.7568	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6671	Approved
0.7552	Intermediate Similarity	NPD422	Phase 1
0.7551	Intermediate Similarity	NPD4908	Phase 1
0.7545	Intermediate Similarity	NPD7473	Discontinued
0.7516	Intermediate Similarity	NPD1934	Approved
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.7515	Intermediate Similarity	NPD8127	Discontinued
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3496	Discontinued
0.747	Intermediate Similarity	NPD6232	Discontinued
0.7469	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4140	Approved
0.7467	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3620	Phase 2
0.7466	Intermediate Similarity	NPD2797	Approved
0.7431	Intermediate Similarity	NPD1610	Phase 2
0.7425	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6674	Discontinued
0.7384	Intermediate Similarity	NPD7549	Discontinued
0.7372	Intermediate Similarity	NPD4110	Phase 3
0.7372	Intermediate Similarity	NPD8166	Discontinued
0.7372	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD2861	Phase 2
0.7342	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7985	Registered
0.7324	Intermediate Similarity	NPD7644	Approved
0.7317	Intermediate Similarity	NPD3817	Phase 2
0.7303	Intermediate Similarity	NPD447	Suspended
0.7303	Intermediate Similarity	NPD5124	Phase 1
0.7303	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD8032	Phase 2
0.7279	Intermediate Similarity	NPD8651	Approved
0.7254	Intermediate Similarity	NPD7340	Approved
0.725	Intermediate Similarity	NPD1512	Approved
0.7246	Intermediate Similarity	NPD4750	Phase 3
0.7209	Intermediate Similarity	NPD7074	Phase 3
0.7197	Intermediate Similarity	NPD1652	Phase 2
0.719	Intermediate Similarity	NPD5735	Approved
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6166	Phase 2
0.7176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4626	Approved
0.7172	Intermediate Similarity	NPD1778	Approved
0.7169	Intermediate Similarity	NPD3882	Suspended
0.7163	Intermediate Similarity	NPD5283	Phase 1
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7151	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD6653	Approved
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3018	Phase 2
0.7126	Intermediate Similarity	NPD7240	Approved
0.7126	Intermediate Similarity	NPD7075	Discontinued
0.7125	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2935	Discontinued
0.711	Intermediate Similarity	NPD7472	Approved
0.7108	Intermediate Similarity	NPD5402	Approved
0.7103	Intermediate Similarity	NPD5585	Approved
0.7102	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3818	Discontinued
0.7092	Intermediate Similarity	NPD5535	Approved
0.7089	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4481	Phase 3
0.7076	Intermediate Similarity	NPD27	Approved
0.7076	Intermediate Similarity	NPD2489	Approved
0.7073	Intermediate Similarity	NPD6599	Discontinued
0.707	Intermediate Similarity	NPD7266	Discontinued
0.7063	Intermediate Similarity	NPD7157	Approved
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD7229	Phase 3
0.7051	Intermediate Similarity	NPD3748	Approved
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3225	Approved
0.7045	Intermediate Similarity	NPD7313	Approved
0.7045	Intermediate Similarity	NPD7312	Approved
0.7045	Intermediate Similarity	NPD7311	Approved
0.7045	Intermediate Similarity	NPD7310	Approved
0.7044	Intermediate Similarity	NPD4628	Phase 3
0.7042	Intermediate Similarity	NPD1398	Phase 1
0.7037	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2237	Approved
0.7012	Intermediate Similarity	NPD3226	Approved
0.7006	Intermediate Similarity	NPD7309	Approved
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD3022	Approved
0.7	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD3266	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7097	Phase 1
0.6986	Remote Similarity	NPD5691	Approved
0.6983	Remote Similarity	NPD7906	Approved
0.698	Remote Similarity	NPD2982	Phase 2
0.698	Remote Similarity	NPD5327	Phase 3
0.698	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2983	Phase 2
0.6975	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7635	Approved
0.6971	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7768	Phase 2
0.6962	Remote Similarity	NPD2346	Discontinued
0.6959	Remote Similarity	NPD1091	Approved
0.6943	Remote Similarity	NPD4308	Phase 3
0.6939	Remote Similarity	NPD17	Approved
0.6937	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2676	Approved
0.6933	Remote Similarity	NPD2675	Approved
0.6932	Remote Similarity	NPD7251	Discontinued
0.6927	Remote Similarity	NPD4663	Approved
0.6927	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD4097	Suspended
0.6919	Remote Similarity	NPD2969	Approved
0.6919	Remote Similarity	NPD2970	Approved
0.6914	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2981	Phase 2
0.6909	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5736	Approved
0.6903	Remote Similarity	NPD1558	Phase 1
0.6899	Remote Similarity	NPD1551	Phase 2
0.6899	Remote Similarity	NPD6032	Approved
0.6893	Remote Similarity	NPD7808	Phase 3
0.6875	Remote Similarity	NPD6797	Phase 2
0.6871	Remote Similarity	NPD2534	Approved
0.6871	Remote Similarity	NPD2532	Approved
0.6871	Remote Similarity	NPD2533	Approved
0.6867	Remote Similarity	NPD4359	Approved
0.6867	Remote Similarity	NPD7028	Phase 2
0.6859	Remote Similarity	NPD230	Phase 1
0.6855	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6005	Phase 3
0.6855	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6002	Phase 3
0.6855	Remote Similarity	NPD6004	Phase 3
0.6854	Remote Similarity	NPD4578	Approved
0.6854	Remote Similarity	NPD4577	Approved
0.6852	Remote Similarity	NPD6666	Approved
0.6852	Remote Similarity	NPD7124	Phase 2
0.6852	Remote Similarity	NPD6667	Approved
0.6848	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3687	Approved
0.6848	Remote Similarity	NPD3686	Approved
0.6846	Remote Similarity	NPD1535	Discovery
0.6846	Remote Similarity	NPD3705	Approved
0.6842	Remote Similarity	NPD4666	Phase 3
0.6836	Remote Similarity	NPD6559	Discontinued
0.6835	Remote Similarity	NPD7033	Discontinued
0.6832	Remote Similarity	NPD3892	Phase 2
0.6829	Remote Similarity	NPD6273	Approved
0.6829	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3453	Discontinued
0.6821	Remote Similarity	NPD1283	Approved
0.6816	Remote Similarity	NPD8054	Approved
0.6816	Remote Similarity	NPD8053	Approved
0.6815	Remote Similarity	NPD6353	Approved
0.681	Remote Similarity	NPD6799	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