NPASS Compound

Structure

CID118266 OpenBabel06191715472D 29 33 0 0 1 0 0 0 0 0999 V2000 -1.1225 -2.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7158 -1.8646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3035 -1.0556 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 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 12 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 17 2 0 0 0 0 8 10 1 0 0 0 0 8 18 2 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 27 2 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 26 1 1 0 0 0 20 25 1 1 0 0 0 21 24 1 0 0 0 0 21 25 1 1 0 0 0 22 23 1 0 0 0 0 22 26 1 1 0 0 0 23 28 1 0 0 0 0 23 29 1 6 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.28
Volume:	433.931
LogP:	6.495
LogD:	4.793
LogS:	-6.841
# Rotatable Bonds:	2
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	4.841
Fsp3:	0.808
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:	-4.559
MDCK Permeability:	2.4121076421579346e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	93.27262878417969%
Volume Distribution (VD):	1.946
Pgp-substrate:	3.590991735458374%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.529
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.26
CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	4.745
Half-life (T1/2):	0.032

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.267
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.769
Skin Sensitization:	0.134
Carcinogencity:	0.209
Eye Corrosion:	0.849
Eye Irritation:	0.286
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC118266

Natural Product ID:	NPC118266
*Common Name:**	Mooloolabene E
IUPAC Name:	[(1S,5aR,7aS,11aS,11bR,13aS,13bR)-8,8,11a,13a-tetramethyl-3,5,5a,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[1,2-g][2]benzofuran-1-yl] acetate
Synonyms:	Mooloolabene E
Standard InCHIKey:	FUWJINVJERRROR-LMZXXRHXSA-N
Standard InCHI:	InChI=1S/C26H38O3/c1-16(27)29-23-22-17(15-28-23)7-9-19-18-8-10-21-24(2,3)12-6-13-25(21,4)20(18)11-14-26(19,22)5/h7-8,19-23H,6,9-15H2,1-5H3/t19-,20-,21-,22+,23-,25+,26-/m0/s1
SMILES:	CC(=O)O[C@@H]1OCC2=CC[C@@H]3[C@]([C@@H]12)(C)CC[C@H]1C3=CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469399
PubChem CID:	11994181
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	Inner Gneerings, a group of shoals off Mooloolaba (Australia)	2005-JUL	PMID[17125226]
NPO21592	Urtica circularis	Species	Urticaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21608987]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7153777]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19439	Calea zacatechichi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21265	Teucrium webbianum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19595	Lathyrus chloranthus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16397	Didymocarpus oblonga	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19735	Euonymus pellucidifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17690	Sideritis sventenii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18198	Selaginella willdenowii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21592	Urtica circularis	Species	Urticaceae	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	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	=	3.0	ug.mL-1	PMID[551286]

☑ 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 NPC118266 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	194
0.1-0.2	1427
0.2-0.3	5868
0.3-0.4	15518
0.4-0.5	8152
0.5-0.6	6408
0.6-0.7	4554
0.7-0.8	537
0.8-0.85	32
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC293044
0.8824	High Similarity	NPC173917
0.8778	High Similarity	NPC94905
0.8778	High Similarity	NPC8954
0.869	High Similarity	NPC472440
0.8681	High Similarity	NPC257726
0.8681	High Similarity	NPC204054
0.8554	High Similarity	NPC473685
0.8488	Intermediate Similarity	NPC472442
0.8352	Intermediate Similarity	NPC88507
0.8333	Intermediate Similarity	NPC65513
0.8316	Intermediate Similarity	NPC134077
0.8298	Intermediate Similarity	NPC228251
0.8298	Intermediate Similarity	NPC20113
0.8298	Intermediate Similarity	NPC477968
0.8298	Intermediate Similarity	NPC161527
0.8298	Intermediate Similarity	NPC477971
0.8298	Intermediate Similarity	NPC219285
0.8298	Intermediate Similarity	NPC477972
0.8261	Intermediate Similarity	NPC471362
0.8261	Intermediate Similarity	NPC471372
0.8261	Intermediate Similarity	NPC472189
0.8256	Intermediate Similarity	NPC469
0.8214	Intermediate Similarity	NPC17550
0.8211	Intermediate Similarity	NPC63249
0.8172	Intermediate Similarity	NPC73858
0.8172	Intermediate Similarity	NPC311166
0.8172	Intermediate Similarity	NPC171598
0.8152	Intermediate Similarity	NPC477722
0.8085	Intermediate Similarity	NPC472188
0.8085	Intermediate Similarity	NPC98112
0.8085	Intermediate Similarity	NPC76266
0.8068	Intermediate Similarity	NPC42586
0.8068	Intermediate Similarity	NPC473251
0.8065	Intermediate Similarity	NPC100892
0.8065	Intermediate Similarity	NPC477970
0.8046	Intermediate Similarity	NPC324243
0.8022	Intermediate Similarity	NPC469403
0.8	Intermediate Similarity	NPC471366
0.8	Intermediate Similarity	NPC318917
0.8	Intermediate Similarity	NPC476800
0.8	Intermediate Similarity	NPC144069
0.8	Intermediate Similarity	NPC472186
0.7979	Intermediate Similarity	NPC112654
0.7978	Intermediate Similarity	NPC286153
0.7957	Intermediate Similarity	NPC104925
0.7957	Intermediate Similarity	NPC189513
0.7957	Intermediate Similarity	NPC298973
0.7957	Intermediate Similarity	NPC469697
0.7917	Intermediate Similarity	NPC473204
0.7917	Intermediate Similarity	NPC472187
0.7917	Intermediate Similarity	NPC473545
0.7907	Intermediate Similarity	NPC195424
0.7872	Intermediate Similarity	NPC230347
0.7872	Intermediate Similarity	NPC275310
0.7872	Intermediate Similarity	NPC135224
0.7872	Intermediate Similarity	NPC477969
0.7872	Intermediate Similarity	NPC286612
0.7849	Intermediate Similarity	NPC166346
0.7826	Intermediate Similarity	NPC273199
0.7822	Intermediate Similarity	NPC112457
0.7812	Intermediate Similarity	NPC473154
0.7791	Intermediate Similarity	NPC153987
0.7791	Intermediate Similarity	NPC44083
0.7791	Intermediate Similarity	NPC242767
0.7789	Intermediate Similarity	NPC162346
0.7789	Intermediate Similarity	NPC319692
0.7789	Intermediate Similarity	NPC325960
0.7778	Intermediate Similarity	NPC244174
0.7766	Intermediate Similarity	NPC324078
0.7755	Intermediate Similarity	NPC238397
0.7755	Intermediate Similarity	NPC471363
0.7753	Intermediate Similarity	NPC96055
0.7753	Intermediate Similarity	NPC71626
0.7753	Intermediate Similarity	NPC318515
0.7742	Intermediate Similarity	NPC477122
0.7742	Intermediate Similarity	NPC165904
0.7742	Intermediate Similarity	NPC179517
0.7732	Intermediate Similarity	NPC477721
0.7732	Intermediate Similarity	NPC477716
0.7727	Intermediate Similarity	NPC471218
0.7717	Intermediate Similarity	NPC470819
0.7717	Intermediate Similarity	NPC177141
0.7717	Intermediate Similarity	NPC470734
0.7717	Intermediate Similarity	NPC473647
0.7711	Intermediate Similarity	NPC476489
0.7711	Intermediate Similarity	NPC12680
0.7711	Intermediate Similarity	NPC476490
0.7708	Intermediate Similarity	NPC477719
0.7708	Intermediate Similarity	NPC477718
0.7701	Intermediate Similarity	NPC233332
0.77	Intermediate Similarity	NPC127790
0.7677	Intermediate Similarity	NPC134270
0.7677	Intermediate Similarity	NPC120009
0.7677	Intermediate Similarity	NPC127933
0.7677	Intermediate Similarity	NPC7644
0.7677	Intermediate Similarity	NPC7613
0.7677	Intermediate Similarity	NPC475889
0.7677	Intermediate Similarity	NPC132395
0.7677	Intermediate Similarity	NPC471365
0.7677	Intermediate Similarity	NPC471364
0.7667	Intermediate Similarity	NPC119001
0.7667	Intermediate Similarity	NPC474013
0.7667	Intermediate Similarity	NPC217394
0.766	Intermediate Similarity	NPC246860
0.766	Intermediate Similarity	NPC163902
0.766	Intermediate Similarity	NPC277721
0.766	Intermediate Similarity	NPC267266
0.766	Intermediate Similarity	NPC471571
0.7654	Intermediate Similarity	NPC476945
0.7653	Intermediate Similarity	NPC477717
0.764	Intermediate Similarity	NPC22611
0.764	Intermediate Similarity	NPC477124
0.7634	Intermediate Similarity	NPC470817
0.7614	Intermediate Similarity	NPC25554
0.7614	Intermediate Similarity	NPC108476
0.7609	Intermediate Similarity	NPC472810
0.7609	Intermediate Similarity	NPC472809
0.7609	Intermediate Similarity	NPC477128
0.7609	Intermediate Similarity	NPC474629
0.76	Intermediate Similarity	NPC264867
0.76	Intermediate Similarity	NPC81567
0.76	Intermediate Similarity	NPC470321
0.76	Intermediate Similarity	NPC473207
0.76	Intermediate Similarity	NPC222161
0.76	Intermediate Similarity	NPC201880
0.7582	Intermediate Similarity	NPC471369
0.7579	Intermediate Similarity	NPC128488
0.7579	Intermediate Similarity	NPC304968
0.7556	Intermediate Similarity	NPC471367
0.7553	Intermediate Similarity	NPC329842
0.7553	Intermediate Similarity	NPC234335
0.7553	Intermediate Similarity	NPC177641
0.7553	Intermediate Similarity	NPC49420
0.7553	Intermediate Similarity	NPC472811
0.7551	Intermediate Similarity	NPC146188
0.7551	Intermediate Similarity	NPC477720
0.7528	Intermediate Similarity	NPC122945
0.7528	Intermediate Similarity	NPC109938
0.7527	Intermediate Similarity	NPC174765
0.7527	Intermediate Similarity	NPC251528
0.7526	Intermediate Similarity	NPC239547
0.7526	Intermediate Similarity	NPC155319
0.7526	Intermediate Similarity	NPC125551
0.7526	Intermediate Similarity	NPC96597
0.7526	Intermediate Similarity	NPC309503
0.7526	Intermediate Similarity	NPC91197
0.7525	Intermediate Similarity	NPC252296
0.7525	Intermediate Similarity	NPC172867
0.7524	Intermediate Similarity	NPC157441
0.75	Intermediate Similarity	NPC281134
0.75	Intermediate Similarity	NPC473369
0.75	Intermediate Similarity	NPC469802
0.75	Intermediate Similarity	NPC166857
0.7475	Intermediate Similarity	NPC121072
0.7475	Intermediate Similarity	NPC21064
0.7474	Intermediate Similarity	NPC472812
0.7474	Intermediate Similarity	NPC470656
0.7473	Intermediate Similarity	NPC329630
0.7473	Intermediate Similarity	NPC30984
0.7471	Intermediate Similarity	NPC4827
0.7451	Intermediate Similarity	NPC88013
0.7451	Intermediate Similarity	NPC125423
0.7451	Intermediate Similarity	NPC109376
0.7451	Intermediate Similarity	NPC184512
0.7447	Intermediate Similarity	NPC159748
0.7447	Intermediate Similarity	NPC212679
0.7447	Intermediate Similarity	NPC220454
0.7447	Intermediate Similarity	NPC101651
0.7447	Intermediate Similarity	NPC477782
0.7447	Intermediate Similarity	NPC159876
0.7447	Intermediate Similarity	NPC469595
0.7444	Intermediate Similarity	NPC132386
0.7429	Intermediate Similarity	NPC194951
0.7429	Intermediate Similarity	NPC12046
0.7426	Intermediate Similarity	NPC476764
0.7426	Intermediate Similarity	NPC476763
0.7423	Intermediate Similarity	NPC164750
0.7419	Intermediate Similarity	NPC93411
0.7419	Intermediate Similarity	NPC24816
0.7419	Intermediate Similarity	NPC473879
0.7416	Intermediate Similarity	NPC290495
0.7416	Intermediate Similarity	NPC229584
0.7416	Intermediate Similarity	NPC195334
0.7416	Intermediate Similarity	NPC14203
0.74	Intermediate Similarity	NPC154452
0.7396	Intermediate Similarity	NPC470255
0.7391	Intermediate Similarity	NPC323209
0.7391	Intermediate Similarity	NPC102996
0.7391	Intermediate Similarity	NPC471368
0.7391	Intermediate Similarity	NPC470050
0.7391	Intermediate Similarity	NPC470051
0.7391	Intermediate Similarity	NPC471219
0.7391	Intermediate Similarity	NPC329692
0.7386	Intermediate Similarity	NPC100906
0.7386	Intermediate Similarity	NPC170561
0.7379	Intermediate Similarity	NPC470024
0.7379	Intermediate Similarity	NPC311223
0.7379	Intermediate Similarity	NPC135015
0.7379	Intermediate Similarity	NPC224660

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 NPC118266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1542
0.2-0.3	4277
0.3-0.4	2233
0.4-0.5	526
0.5-0.6	250
0.6-0.7	138
0.7-0.8	13
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
0.7527	Intermediate Similarity	NPD6051	Approved
0.7333	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6686	Approved
0.7021	Intermediate Similarity	NPD7521	Approved
0.7021	Intermediate Similarity	NPD7334	Approved
0.7021	Intermediate Similarity	NPD5330	Approved
0.7021	Intermediate Similarity	NPD7146	Approved
0.7021	Intermediate Similarity	NPD6409	Approved
0.7021	Intermediate Similarity	NPD6684	Approved
0.6989	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6399	Phase 3
0.6875	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD6903	Approved
0.6786	Remote Similarity	NPD7328	Approved
0.6786	Remote Similarity	NPD7327	Approved
0.6765	Remote Similarity	NPD7638	Approved
0.6754	Remote Similarity	NPD8033	Approved
0.6754	Remote Similarity	NPD7503	Approved
0.6747	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8039	Approved
0.6737	Remote Similarity	NPD1694	Approved
0.6726	Remote Similarity	NPD7516	Approved
0.67	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7900	Approved
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD6412	Phase 2
0.6609	Remote Similarity	NPD8379	Approved
0.6609	Remote Similarity	NPD8378	Approved
0.6609	Remote Similarity	NPD8335	Approved
0.6609	Remote Similarity	NPD8296	Approved
0.6609	Remote Similarity	NPD8380	Approved
0.6602	Remote Similarity	NPD4225	Approved
0.6556	Remote Similarity	NPD6942	Approved
0.6556	Remote Similarity	NPD7339	Approved
0.6535	Remote Similarity	NPD7748	Approved
0.6505	Remote Similarity	NPD7902	Approved
0.6484	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD6080	Approved
0.6465	Remote Similarity	NPD6904	Approved
0.6458	Remote Similarity	NPD4786	Approved
0.6452	Remote Similarity	NPD7645	Phase 2
0.6429	Remote Similarity	NPD3573	Approved
0.6421	Remote Similarity	NPD3667	Approved
0.64	Remote Similarity	NPD5207	Approved
0.6387	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD5208	Approved
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6083	Phase 2
0.6346	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD7515	Phase 2
0.6337	Remote Similarity	NPD6050	Approved
0.6311	Remote Similarity	NPD5695	Phase 3
0.63	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3668	Phase 3
0.6283	Remote Similarity	NPD8133	Approved
0.6264	Remote Similarity	NPD4785	Approved
0.6264	Remote Similarity	NPD4784	Approved
0.6261	Remote Similarity	NPD7115	Discovery
0.6239	Remote Similarity	NPD6008	Approved
0.6238	Remote Similarity	NPD5692	Phase 3
0.623	Remote Similarity	NPD7319	Approved
0.6222	Remote Similarity	NPD4243	Approved
0.6214	Remote Similarity	NPD6001	Approved
0.6211	Remote Similarity	NPD7525	Registered
0.6195	Remote Similarity	NPD6882	Approved
0.6176	Remote Similarity	NPD7637	Suspended
0.6176	Remote Similarity	NPD8034	Phase 2
0.6176	Remote Similarity	NPD6411	Approved
0.6176	Remote Similarity	NPD5694	Approved
0.6176	Remote Similarity	NPD8035	Phase 2
0.6132	Remote Similarity	NPD5696	Approved
0.6122	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3665	Phase 1
0.6122	Remote Similarity	NPD3133	Approved
0.6122	Remote Similarity	NPD3666	Approved
0.6111	Remote Similarity	NPD7632	Discontinued
0.6105	Remote Similarity	NPD4195	Approved
0.61	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7732	Phase 3
0.6092	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5739	Approved
0.6091	Remote Similarity	NPD6675	Approved
0.6091	Remote Similarity	NPD7128	Approved
0.6091	Remote Similarity	NPD6402	Approved
0.6087	Remote Similarity	NPD6926	Approved
0.6087	Remote Similarity	NPD6924	Approved
0.6061	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5707	Approved
0.605	Remote Similarity	NPD8515	Approved
0.605	Remote Similarity	NPD8513	Phase 3
0.605	Remote Similarity	NPD8517	Approved
0.605	Remote Similarity	NPD8516	Approved
0.6036	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD8264	Approved
0.602	Remote Similarity	NPD6695	Phase 3
0.6019	Remote Similarity	NPD5281	Approved
0.6019	Remote Similarity	NPD5284	Approved
0.6016	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD1145	Discontinued
0.6	Remote Similarity	NPD3618	Phase 1
0.5983	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6881	Approved
0.5982	Remote Similarity	NPD6899	Approved
0.5982	Remote Similarity	NPD7320	Approved
0.598	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5328	Approved
0.598	Remote Similarity	NPD6101	Approved
0.5965	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5779	Approved
0.5962	Remote Similarity	NPD5778	Approved
0.5957	Remote Similarity	NPD6933	Approved
0.595	Remote Similarity	NPD8328	Phase 3
0.5943	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6929	Approved
0.5935	Remote Similarity	NPD8293	Discontinued
0.5929	Remote Similarity	NPD6372	Approved
0.5929	Remote Similarity	NPD6373	Approved
0.5929	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6404	Discontinued
0.5918	Remote Similarity	NPD4223	Phase 3
0.5918	Remote Similarity	NPD4221	Approved
0.5913	Remote Similarity	NPD6053	Discontinued
0.5909	Remote Similarity	NPD6052	Approved
0.59	Remote Similarity	NPD5329	Approved
0.59	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5701	Approved
0.5893	Remote Similarity	NPD5697	Approved
0.5877	Remote Similarity	NPD6883	Approved
0.5877	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD7290	Approved
0.5877	Remote Similarity	NPD7102	Approved
0.5876	Remote Similarity	NPD6931	Approved
0.5876	Remote Similarity	NPD6930	Phase 2
0.5876	Remote Similarity	NPD4695	Discontinued
0.5876	Remote Similarity	NPD7509	Discontinued
0.5868	Remote Similarity	NPD6370	Approved
0.5865	Remote Similarity	NPD6079	Approved
0.5851	Remote Similarity	NPD4190	Phase 3
0.5851	Remote Similarity	NPD5275	Approved
0.5849	Remote Similarity	NPD5654	Approved
0.5842	Remote Similarity	NPD5279	Phase 3
0.5841	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6650	Approved
0.5826	Remote Similarity	NPD6847	Approved
0.5826	Remote Similarity	NPD8130	Phase 1
0.5826	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6649	Approved
0.5826	Remote Similarity	NPD6617	Approved
0.5826	Remote Similarity	NPD6869	Approved
0.5825	Remote Similarity	NPD4753	Phase 2
0.5824	Remote Similarity	NPD6923	Approved
0.5824	Remote Similarity	NPD6922	Approved
0.5824	Remote Similarity	NPD4137	Phase 3
0.582	Remote Similarity	NPD6067	Discontinued
0.581	Remote Similarity	NPD4202	Approved
0.58	Remote Similarity	NPD4197	Approved
0.5794	Remote Similarity	NPD7614	Phase 1
0.5789	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD6014	Approved
0.5789	Remote Similarity	NPD6012	Approved
0.5784	Remote Similarity	NPD7750	Discontinued
0.5784	Remote Similarity	NPD7524	Approved
0.578	Remote Similarity	NPD6648	Approved
0.5776	Remote Similarity	NPD8297	Approved
0.5772	Remote Similarity	NPD7492	Approved
0.5761	Remote Similarity	NPD7143	Approved
0.5761	Remote Similarity	NPD4691	Approved
0.5761	Remote Similarity	NPD4747	Approved
0.5761	Remote Similarity	NPD7144	Approved
0.5758	Remote Similarity	NPD5209	Approved
0.5745	Remote Similarity	NPD5733	Approved
0.5741	Remote Similarity	NPD5959	Approved
0.5729	Remote Similarity	NPD6925	Approved
0.5729	Remote Similarity	NPD5776	Phase 2
0.5727	Remote Similarity	NPD5344	Discontinued
0.5726	Remote Similarity	NPD7094	Approved
0.5726	Remote Similarity	NPD6858	Approved
0.5726	Remote Similarity	NPD6616	Approved
0.5714	Remote Similarity	NPD7514	Phase 3
0.5714	Remote Similarity	NPD4748	Discontinued
0.5714	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7332	Phase 2
0.5702	Remote Similarity	NPD6059	Approved
0.5702	Remote Similarity	NPD6054	Approved
0.5701	Remote Similarity	NPD1698	Clinical (unspecified phase)

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