NPASS Compound

Structure

CID293044 OpenBabel06191716102D 33 37 0 0 1 0 0 0 0 0999 V2000 7.6010 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 1.5388 -1.5000 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 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 3.2709 0.5000 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 5.0029 -0.5000 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 7.6010 -1.0000 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 -1.0000 0.0000 C 0 0 2 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 5.8690 -2.0000 0.0000 C 0 0 1 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 2.4049 -1.0000 0.0000 C 0 0 2 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 8.4670 -0.5000 0.0000 O 0 0 0 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 6.7350 -0.5000 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 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 26 1 0 0 0 0 12 28 1 0 0 0 0 13 27 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 31 1 0 0 0 0 16 29 2 0 0 0 0 16 32 1 0 0 0 0 17 30 2 0 0 0 0 17 33 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 27 1 1 0 0 0 21 28 1 1 0 0 0 22 24 1 0 0 0 0 22 32 1 1 0 0 0 23 25 1 0 0 0 0 23 27 1 1 0 0 0 24 26 1 0 0 0 0 24 28 1 1 0 0 0 25 31 1 0 0 0 0 25 33 1 6 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.29
Volume:	483.467
LogP:	5.8
LogD:	4.457
LogS:	-6.109
# Rotatable Bonds:	4
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	5.115
Fsp3:	0.786
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:	-4.633
MDCK Permeability:	2.690898509172257e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.12
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	85.94341278076172%
Volume Distribution (VD):	2.102
Pgp-substrate:	6.245518207550049%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.445
CYP2C9-inhibitor:	0.319
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.18
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.624
CYP3A4-substrate:	0.309

ADMET: Excretion

Clearance (CL):	2.552
Half-life (T1/2):	0.048

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.67
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.67
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.152
Carcinogencity:	0.075
Eye Corrosion:	0.47
Eye Irritation:	0.053
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC293044

Natural Product ID:	NPC293044
*Common Name:**	Mooloolabene D
IUPAC Name:	[(1S,5aR,7R,7aS,11aR,11bR,13aS,13bR)-1-acetyloxy-8,8,11a,13a-tetramethyl-3,5,5a,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-7-yl] acetate
Synonyms:	Mooloolabene D
Standard InCHIKey:	JCJGAZKXOUBQBW-GNVPTIMCSA-N
Standard InCHI:	InChI=1S/C28H40O5/c1-16(29)32-22-14-19-20-9-8-18-15-31-25(33-17(2)30)23(18)27(20,5)13-10-21(19)28(6)12-7-11-26(3,4)24(22)28/h8,14,20-25H,7,9-13,15H2,1-6H3/t20-,21-,22+,23+,24-,25-,27-,28+/m0/s1
SMILES:	CC(=O)O[C@@H]1C=C2[C@@H]3CC=C4CO[C@H]([C@@H]4[C@@]3(C)CC[C@@H]2[C@@]2(C)CCCC(C)(C)[C@H]12)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511608
PubChem CID:	11994178
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]
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]
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]

☑ 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[482329]

☑ 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 NPC293044 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	200
0.1-0.2	1321
0.2-0.3	5234
0.3-0.4	14808
0.4-0.5	8194
0.5-0.6	6410
0.6-0.7	5510
0.7-0.8	947
0.8-0.85	68
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC118266
0.9111	High Similarity	NPC94905
0.9111	High Similarity	NPC8954
0.8681	High Similarity	NPC88507
0.8621	High Similarity	NPC472442
0.8617	High Similarity	NPC161527
0.8617	High Similarity	NPC219285
0.8617	High Similarity	NPC228251
0.8617	High Similarity	NPC477971
0.8617	High Similarity	NPC477968
0.8617	High Similarity	NPC477972
0.8617	High Similarity	NPC20113
0.8605	High Similarity	NPC472440
0.8602	High Similarity	NPC257726
0.8602	High Similarity	NPC204054
0.8587	High Similarity	NPC471372
0.8587	High Similarity	NPC471362
0.8587	High Similarity	NPC472189
0.8523	High Similarity	NPC173917
0.8495	Intermediate Similarity	NPC311166
0.8495	Intermediate Similarity	NPC171598
0.8478	Intermediate Similarity	NPC477722
0.8471	Intermediate Similarity	NPC473685
0.8404	Intermediate Similarity	NPC98112
0.8404	Intermediate Similarity	NPC472188
0.8352	Intermediate Similarity	NPC469403
0.8333	Intermediate Similarity	NPC144069
0.8316	Intermediate Similarity	NPC471366
0.8316	Intermediate Similarity	NPC476800
0.8316	Intermediate Similarity	NPC472186
0.8316	Intermediate Similarity	NPC318917
0.8315	Intermediate Similarity	NPC286153
0.8298	Intermediate Similarity	NPC112654
0.828	Intermediate Similarity	NPC104925
0.828	Intermediate Similarity	NPC298973
0.828	Intermediate Similarity	NPC469697
0.8261	Intermediate Similarity	NPC65513
0.8247	Intermediate Similarity	NPC134077
0.8229	Intermediate Similarity	NPC472187
0.8229	Intermediate Similarity	NPC473545
0.8229	Intermediate Similarity	NPC473204
0.8191	Intermediate Similarity	NPC230347
0.8191	Intermediate Similarity	NPC100892
0.8191	Intermediate Similarity	NPC135224
0.8191	Intermediate Similarity	NPC275310
0.8191	Intermediate Similarity	NPC286612
0.8191	Intermediate Similarity	NPC477970
0.8191	Intermediate Similarity	NPC477969
0.8144	Intermediate Similarity	NPC63249
0.8125	Intermediate Similarity	NPC473154
0.8119	Intermediate Similarity	NPC112457
0.8105	Intermediate Similarity	NPC73858
0.8105	Intermediate Similarity	NPC162346
0.8085	Intermediate Similarity	NPC189513
0.8068	Intermediate Similarity	NPC471218
0.8061	Intermediate Similarity	NPC471363
0.8061	Intermediate Similarity	NPC238397
0.8043	Intermediate Similarity	NPC470819
0.8043	Intermediate Similarity	NPC470734
0.8043	Intermediate Similarity	NPC177141
0.8041	Intermediate Similarity	NPC477716
0.8041	Intermediate Similarity	NPC477721
0.8021	Intermediate Similarity	NPC477719
0.8021	Intermediate Similarity	NPC76266
0.8021	Intermediate Similarity	NPC477718
0.8	Intermediate Similarity	NPC474013
0.798	Intermediate Similarity	NPC471364
0.798	Intermediate Similarity	NPC120009
0.798	Intermediate Similarity	NPC127933
0.798	Intermediate Similarity	NPC134270
0.798	Intermediate Similarity	NPC132395
0.798	Intermediate Similarity	NPC7644
0.798	Intermediate Similarity	NPC475889
0.798	Intermediate Similarity	NPC7613
0.798	Intermediate Similarity	NPC471365
0.7979	Intermediate Similarity	NPC163902
0.7979	Intermediate Similarity	NPC471571
0.7979	Intermediate Similarity	NPC246860
0.7978	Intermediate Similarity	NPC324243
0.7978	Intermediate Similarity	NPC469
0.7959	Intermediate Similarity	NPC477717
0.7957	Intermediate Similarity	NPC273199
0.7957	Intermediate Similarity	NPC470817
0.7955	Intermediate Similarity	NPC25554
0.7935	Intermediate Similarity	NPC474629
0.7935	Intermediate Similarity	NPC477128
0.7935	Intermediate Similarity	NPC472809
0.7935	Intermediate Similarity	NPC472810
0.7931	Intermediate Similarity	NPC17550
0.7931	Intermediate Similarity	NPC242767
0.7931	Intermediate Similarity	NPC44083
0.7931	Intermediate Similarity	NPC153987
0.7912	Intermediate Similarity	NPC471369
0.79	Intermediate Similarity	NPC264867
0.79	Intermediate Similarity	NPC470321
0.79	Intermediate Similarity	NPC81567
0.79	Intermediate Similarity	NPC473207
0.79	Intermediate Similarity	NPC222161
0.79	Intermediate Similarity	NPC201880
0.7895	Intermediate Similarity	NPC128488
0.7895	Intermediate Similarity	NPC304968
0.7889	Intermediate Similarity	NPC471367
0.7889	Intermediate Similarity	NPC96055
0.7872	Intermediate Similarity	NPC234335
0.7872	Intermediate Similarity	NPC177641
0.7872	Intermediate Similarity	NPC329842
0.7872	Intermediate Similarity	NPC472811
0.7857	Intermediate Similarity	NPC146188
0.7849	Intermediate Similarity	NPC473647
0.7841	Intermediate Similarity	NPC233332
0.7841	Intermediate Similarity	NPC469802
0.7835	Intermediate Similarity	NPC239547
0.7835	Intermediate Similarity	NPC91197
0.7835	Intermediate Similarity	NPC125551
0.7835	Intermediate Similarity	NPC96597
0.7835	Intermediate Similarity	NPC309503
0.7835	Intermediate Similarity	NPC155319
0.7826	Intermediate Similarity	NPC166857
0.7822	Intermediate Similarity	NPC172867
0.7822	Intermediate Similarity	NPC127790
0.7822	Intermediate Similarity	NPC252296
0.7812	Intermediate Similarity	NPC473369
0.7812	Intermediate Similarity	NPC281134
0.781	Intermediate Similarity	NPC157441
0.7802	Intermediate Similarity	NPC42586
0.7802	Intermediate Similarity	NPC473251
0.7802	Intermediate Similarity	NPC119001
0.7789	Intermediate Similarity	NPC472812
0.7778	Intermediate Similarity	NPC121072
0.7778	Intermediate Similarity	NPC21064
0.7778	Intermediate Similarity	NPC132386
0.7766	Intermediate Similarity	NPC469595
0.7766	Intermediate Similarity	NPC212679
0.7766	Intermediate Similarity	NPC220454
0.7766	Intermediate Similarity	NPC159876
0.7753	Intermediate Similarity	NPC108476
0.7745	Intermediate Similarity	NPC109376
0.7745	Intermediate Similarity	NPC88013
0.7745	Intermediate Similarity	NPC184512
0.7745	Intermediate Similarity	NPC125423
0.7742	Intermediate Similarity	NPC93411
0.7742	Intermediate Similarity	NPC473879
0.7732	Intermediate Similarity	NPC319692
0.7732	Intermediate Similarity	NPC164750
0.7732	Intermediate Similarity	NPC325960
0.7717	Intermediate Similarity	NPC102996
0.7717	Intermediate Similarity	NPC471368
0.7717	Intermediate Similarity	NPC244174
0.7714	Intermediate Similarity	NPC12046
0.7714	Intermediate Similarity	NPC194951
0.7708	Intermediate Similarity	NPC470255
0.7708	Intermediate Similarity	NPC324078
0.77	Intermediate Similarity	NPC154452
0.7692	Intermediate Similarity	NPC71626
0.7692	Intermediate Similarity	NPC319238
0.7692	Intermediate Similarity	NPC318515
0.7684	Intermediate Similarity	NPC474631
0.7684	Intermediate Similarity	NPC165904
0.7684	Intermediate Similarity	NPC49420
0.7684	Intermediate Similarity	NPC120539
0.7684	Intermediate Similarity	NPC179517
0.7684	Intermediate Similarity	NPC477122
0.7677	Intermediate Similarity	NPC324841
0.767	Intermediate Similarity	NPC135015
0.767	Intermediate Similarity	NPC217921
0.767	Intermediate Similarity	NPC48548
0.767	Intermediate Similarity	NPC470024
0.767	Intermediate Similarity	NPC128795
0.767	Intermediate Similarity	NPC224660
0.767	Intermediate Similarity	NPC311223
0.7667	Intermediate Similarity	NPC122945
0.7667	Intermediate Similarity	NPC286786
0.7667	Intermediate Similarity	NPC109938
0.766	Intermediate Similarity	NPC174765
0.766	Intermediate Similarity	NPC473058
0.7653	Intermediate Similarity	NPC10057
0.7653	Intermediate Similarity	NPC97867
0.7647	Intermediate Similarity	NPC218158
0.764	Intermediate Similarity	NPC269791
0.764	Intermediate Similarity	NPC195424
0.7634	Intermediate Similarity	NPC102640
0.7629	Intermediate Similarity	NPC474909
0.7629	Intermediate Similarity	NPC472441
0.7624	Intermediate Similarity	NPC254202
0.7609	Intermediate Similarity	NPC35933
0.7604	Intermediate Similarity	NPC267266
0.7604	Intermediate Similarity	NPC169343
0.7604	Intermediate Similarity	NPC277721
0.7604	Intermediate Similarity	NPC166346
0.76	Intermediate Similarity	NPC285231
0.76	Intermediate Similarity	NPC473384
0.76	Intermediate Similarity	NPC21568
0.76	Intermediate Similarity	NPC280991
0.7596	Intermediate Similarity	NPC206618
0.7596	Intermediate Similarity	NPC316974
0.7596	Intermediate Similarity	NPC40728
0.7582	Intermediate Similarity	NPC474193
0.7582	Intermediate Similarity	NPC12283
0.7582	Intermediate Similarity	NPC477124
0.7582	Intermediate Similarity	NPC49208

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 NPC293044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1471
0.2-0.3	4106
0.3-0.4	2385
0.4-0.5	583
0.5-0.6	238
0.6-0.7	180
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7849	Intermediate Similarity	NPD6051	Approved
0.7333	Intermediate Similarity	NPD6686	Approved
0.7312	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6399	Phase 3
0.7188	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6684	Approved
0.7158	Intermediate Similarity	NPD7521	Approved
0.7158	Intermediate Similarity	NPD7334	Approved
0.7158	Intermediate Similarity	NPD7146	Approved
0.7158	Intermediate Similarity	NPD5330	Approved
0.7158	Intermediate Similarity	NPD6409	Approved
0.7059	Intermediate Similarity	NPD7638	Approved
0.7054	Intermediate Similarity	NPD7328	Approved
0.7054	Intermediate Similarity	NPD7327	Approved
0.7018	Intermediate Similarity	NPD8033	Approved
0.7018	Intermediate Similarity	NPD7503	Approved
0.701	Intermediate Similarity	NPD6672	Approved
0.701	Intermediate Similarity	NPD5737	Approved
0.701	Intermediate Similarity	NPD6903	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7900	Approved
0.6991	Remote Similarity	NPD7516	Approved
0.699	Remote Similarity	NPD7640	Approved
0.699	Remote Similarity	NPD7639	Approved
0.693	Remote Similarity	NPD8294	Approved
0.693	Remote Similarity	NPD8377	Approved
0.6916	Remote Similarity	NPD6412	Phase 2
0.6893	Remote Similarity	NPD4225	Approved
0.6875	Remote Similarity	NPD1694	Approved
0.687	Remote Similarity	NPD8379	Approved
0.687	Remote Similarity	NPD8378	Approved
0.687	Remote Similarity	NPD8296	Approved
0.687	Remote Similarity	NPD8380	Approved
0.687	Remote Similarity	NPD8335	Approved
0.6832	Remote Similarity	NPD7748	Approved
0.68	Remote Similarity	NPD5693	Phase 1
0.6796	Remote Similarity	NPD7902	Approved
0.6703	Remote Similarity	NPD7339	Approved
0.6703	Remote Similarity	NPD6942	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7515	Phase 2
0.6633	Remote Similarity	NPD6098	Approved
0.663	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6080	Approved
0.66	Remote Similarity	NPD6673	Approved
0.66	Remote Similarity	NPD6904	Approved
0.6598	Remote Similarity	NPD3668	Phase 3
0.6598	Remote Similarity	NPD4786	Approved
0.6596	Remote Similarity	NPD7645	Phase 2
0.6562	Remote Similarity	NPD3667	Approved
0.6549	Remote Similarity	NPD8133	Approved
0.6526	Remote Similarity	NPD7525	Registered
0.6522	Remote Similarity	NPD8039	Approved
0.6522	Remote Similarity	NPD7115	Discovery
0.6514	Remote Similarity	NPD6008	Approved
0.6512	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6083	Phase 2
0.6476	Remote Similarity	NPD6084	Phase 2
0.6475	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD6050	Approved
0.6471	Remote Similarity	NPD7637	Suspended
0.6471	Remote Similarity	NPD8035	Phase 2
0.646	Remote Similarity	NPD6882	Approved
0.6442	Remote Similarity	NPD5695	Phase 3
0.6436	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3573	Approved
0.6389	Remote Similarity	NPD7632	Discontinued
0.6373	Remote Similarity	NPD5692	Phase 3
0.6373	Remote Similarity	NPD5207	Approved
0.6364	Remote Similarity	NPD5739	Approved
0.6364	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD7128	Approved
0.6364	Remote Similarity	NPD6402	Approved
0.6337	Remote Similarity	NPD5208	Approved
0.6327	Remote Similarity	NPD6695	Phase 3
0.6311	Remote Similarity	NPD5694	Approved
0.6306	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8517	Approved
0.6303	Remote Similarity	NPD8515	Approved
0.6303	Remote Similarity	NPD8513	Phase 3
0.6303	Remote Similarity	NPD8516	Approved
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD3133	Approved
0.6263	Remote Similarity	NPD3666	Approved
0.6263	Remote Similarity	NPD3665	Phase 1
0.6262	Remote Similarity	NPD5696	Approved
0.626	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4785	Approved
0.6237	Remote Similarity	NPD6924	Approved
0.6237	Remote Similarity	NPD4784	Approved
0.6237	Remote Similarity	NPD6926	Approved
0.6228	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7732	Phase 3
0.62	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD8328	Phase 3
0.6196	Remote Similarity	NPD4243	Approved
0.6195	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6372	Approved
0.6195	Remote Similarity	NPD6373	Approved
0.619	Remote Similarity	NPD6001	Approved
0.6179	Remote Similarity	NPD8293	Discontinued
0.6174	Remote Similarity	NPD6053	Discontinued
0.617	Remote Similarity	NPD8264	Approved
0.6161	Remote Similarity	NPD5697	Approved
0.6161	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD5284	Approved
0.614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6883	Approved
0.614	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD3618	Phase 1
0.6117	Remote Similarity	NPD5328	Approved
0.6116	Remote Similarity	NPD6370	Approved
0.6111	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6011	Approved
0.6105	Remote Similarity	NPD6933	Approved
0.6087	Remote Similarity	NPD6617	Approved
0.6087	Remote Similarity	NPD8130	Phase 1
0.6087	Remote Similarity	NPD6649	Approved
0.6087	Remote Similarity	NPD6847	Approved
0.6087	Remote Similarity	NPD6869	Approved
0.6087	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6650	Approved
0.6082	Remote Similarity	NPD6929	Approved
0.6082	Remote Similarity	NPD4195	Approved
0.6078	Remote Similarity	NPD7750	Discontinued
0.6078	Remote Similarity	NPD7524	Approved
0.6075	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6067	Discontinued
0.6061	Remote Similarity	NPD5209	Approved
0.6055	Remote Similarity	NPD6648	Approved
0.6053	Remote Similarity	NPD6014	Approved
0.6053	Remote Similarity	NPD6013	Approved
0.6053	Remote Similarity	NPD6012	Approved
0.6038	Remote Similarity	NPD5707	Approved
0.6036	Remote Similarity	NPD6052	Approved
0.6034	Remote Similarity	NPD8297	Approved
0.602	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6930	Phase 2
0.602	Remote Similarity	NPD4695	Discontinued
0.602	Remote Similarity	NPD7509	Discontinued
0.602	Remote Similarity	NPD6931	Approved
0.6016	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD5344	Discontinued
0.5981	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5654	Approved
0.598	Remote Similarity	NPD5279	Phase 3
0.598	Remote Similarity	NPD4519	Discontinued
0.598	Remote Similarity	NPD4623	Approved
0.5979	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6923	Approved
0.5978	Remote Similarity	NPD6922	Approved
0.5977	Remote Similarity	NPD1145	Discontinued
0.5968	Remote Similarity	NPD6616	Approved
0.5966	Remote Similarity	NPD6009	Approved
0.5962	Remote Similarity	NPD4753	Phase 2
0.595	Remote Similarity	NPD6054	Approved
0.595	Remote Similarity	NPD6059	Approved
0.5943	Remote Similarity	NPD4202	Approved
0.5935	Remote Similarity	NPD7122	Discontinued
0.5926	Remote Similarity	NPD7614	Phase 1
0.592	Remote Similarity	NPD7078	Approved
0.5914	Remote Similarity	NPD7144	Approved
0.5914	Remote Similarity	NPD7143	Approved
0.5905	Remote Similarity	NPD7838	Discovery
0.5905	Remote Similarity	NPD46	Approved
0.5905	Remote Similarity	NPD5785	Approved
0.5905	Remote Similarity	NPD6698	Approved
0.59	Remote Similarity	NPD4223	Phase 3
0.59	Remote Similarity	NPD4221	Approved
0.5882	Remote Similarity	NPD5329	Approved
0.5876	Remote Similarity	NPD5776	Phase 2
0.5876	Remote Similarity	NPD6925	Approved
0.5872	Remote Similarity	NPD4755	Approved
0.5872	Remote Similarity	NPD5959	Approved
0.5859	Remote Similarity	NPD4821	Approved
0.5859	Remote Similarity	NPD4820	Approved
0.5859	Remote Similarity	NPD7332	Phase 2
0.5859	Remote Similarity	NPD4748	Discontinued
0.5859	Remote Similarity	NPD4819	Approved
0.5859	Remote Similarity	NPD7514	Phase 3
0.5859	Remote Similarity	NPD4822	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