NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	518.29
Volume:	527.134
LogP:	4.325
LogD:	3.896
LogS:	-4.811
# Rotatable Bonds:	6
TPSA:	115.43
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	5.11
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.332
MDCK Permeability:	3.0661623895866796e-05
Pgp-inhibitor:	0.358
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	92.02442169189453%
Volume Distribution (VD):	0.809
Pgp-substrate:	5.293799877166748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.451
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.405
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	3.067
Half-life (T1/2):	0.529

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.406
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.232
Maximum Recommended Daily Dose:	0.662
Skin Sensitization:	0.552
Carcinogencity:	0.289
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC477717

Natural Product ID:	NPC477717
*Common Name:**	Petrosaspongiolide N
IUPAC Name:	[(1S,3R,4aR,4bS,6aR,7S,10aR,10bS,12aS)-1-acetyloxy-3-(2-hydroxy-5-oxo-2H-furan-3-yl)-4b,7,10a-trimethyl-1,3,4,4a,5,6,6a,8,9,10,10b,11,12,12a-tetradecahydronaphtho[2,1-f]isochromen-7-yl]methyl acetate
Synonyms:	Petrosaspongiolide N
Standard InCHIKey:	ZSDRTHXMHGHLMW-VEIQJVNDSA-N
Standard InCHI:	InChI=1S/C29H42O8/c1-16(30)34-15-27(3)10-6-11-29(5)22(27)9-12-28(4)20-14-21(19-13-24(32)37-25(19)33)36-26(35-17(2)31)18(20)7-8-23(28)29/h13,18,20-23,25-26,33H,6-12,14-15H2,1-5H3/t18-,20+,21+,22-,23-,25?,26+,27+,28-,29-/m0/s1
SMILES:	CC(=O)OC[C@]1(CCC[C@]2([C@H]1CC[C@@]3([C@@H]2CC[C@H]4[C@H]3C[C@@H](O[C@H]4OC(=O)C)C5=CC(=O)OC5O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44575490
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO3351	Petrosaspongia nigra	Species	Thorectidae	Eukaryota	n.a.	the southern coast of New Caledonia	1987-NOV; 1988-DEC	PMID[9599251]
NPO3351	Petrosaspongia nigra	Species	Thorectidae	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
Others	4

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	Activity	=	43.9	%	PMID[9599251]
NPT2586	Individual Protein	Phospholipase A2, acidic	Naja naja	Activity	=	6.8	%	PMID[9599251]
NPT545	Individual Protein	Phospholipase A2 group 1B	Homo sapiens	Activity	=	44	%	PMID[9599251]
NPT2	Others	Unspecified		Activity	=	11.6	%	PMID[9599251]

☑ 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 NPC477717 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	209
0.1-0.2	1473
0.2-0.3	4699
0.3-0.4	11169
0.4-0.5	10995
0.5-0.6	6987
0.6-0.7	4760
0.7-0.8	2172
0.8-0.85	206
0.85-0.9	18
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC477721
0.9892	High Similarity	NPC477716
0.9677	High Similarity	NPC477718
0.9677	High Similarity	NPC477719
0.9355	High Similarity	NPC477722
0.8947	High Similarity	NPC469697
0.8835	High Similarity	NPC476766
0.8817	High Similarity	NPC472809
0.8817	High Similarity	NPC472810
0.8776	High Similarity	NPC325229
0.8776	High Similarity	NPC275086
0.8763	High Similarity	NPC162346
0.875	High Similarity	NPC104925
0.875	High Similarity	NPC298973
0.8738	High Similarity	NPC476759
0.8723	High Similarity	NPC470734
0.8687	High Similarity	NPC324841
0.8673	High Similarity	NPC51499
0.8641	High Similarity	NPC476765
0.8641	High Similarity	NPC177524
0.8641	High Similarity	NPC219900
0.8641	High Similarity	NPC392
0.8617	High Similarity	NPC474629
0.8614	High Similarity	NPC45897
0.8614	High Similarity	NPC281378
0.8598	High Similarity	NPC5311
0.8598	High Similarity	NPC310341
0.8598	High Similarity	NPC199428
0.8598	High Similarity	NPC99620
0.8598	High Similarity	NPC193382
0.8585	High Similarity	NPC473159
0.8558	High Similarity	NPC475030
0.8557	High Similarity	NPC324078
0.8544	High Similarity	NPC471205
0.8542	High Similarity	NPC329842
0.8519	High Similarity	NPC244402
0.8519	High Similarity	NPC152615
0.8519	High Similarity	NPC99728
0.8519	High Similarity	NPC158344
0.8519	High Similarity	NPC473852
0.8519	High Similarity	NPC471353
0.8519	High Similarity	NPC77319
0.8519	High Similarity	NPC243196
0.8519	High Similarity	NPC27507
0.8519	High Similarity	NPC50305
0.8519	High Similarity	NPC87250
0.8519	High Similarity	NPC309034
0.8519	High Similarity	NPC34390
0.8519	High Similarity	NPC196429
0.8519	High Similarity	NPC471351
0.8519	High Similarity	NPC474418
0.8519	High Similarity	NPC142066
0.8519	High Similarity	NPC93883
0.8519	High Similarity	NPC471355
0.8519	High Similarity	NPC84987
0.8519	High Similarity	NPC471354
0.8519	High Similarity	NPC157376
0.8515	High Similarity	NPC121423
0.8505	High Similarity	NPC84949
0.8505	High Similarity	NPC69576
0.8505	High Similarity	NPC471633
0.8505	High Similarity	NPC31354
0.85	High Similarity	NPC228251
0.85	High Similarity	NPC477971
0.85	High Similarity	NPC477972
0.85	High Similarity	NPC161527
0.85	High Similarity	NPC477968
0.85	High Similarity	NPC219285
0.85	High Similarity	NPC20113
0.8454	Intermediate Similarity	NPC472812
0.8447	Intermediate Similarity	NPC476760
0.8447	Intermediate Similarity	NPC51719
0.8447	Intermediate Similarity	NPC218158
0.8447	Intermediate Similarity	NPC476761
0.8447	Intermediate Similarity	NPC476762
0.844	Intermediate Similarity	NPC83287
0.8431	Intermediate Similarity	NPC120009
0.8416	Intermediate Similarity	NPC198992
0.8416	Intermediate Similarity	NPC11974
0.8381	Intermediate Similarity	NPC206618
0.8378	Intermediate Similarity	NPC40749
0.8365	Intermediate Similarity	NPC122816
0.8364	Intermediate Similarity	NPC5883
0.8364	Intermediate Similarity	NPC329905
0.8364	Intermediate Similarity	NPC236973
0.8364	Intermediate Similarity	NPC469756
0.8364	Intermediate Similarity	NPC29639
0.8364	Intermediate Similarity	NPC32177
0.8364	Intermediate Similarity	NPC304260
0.8364	Intermediate Similarity	NPC55532
0.8364	Intermediate Similarity	NPC30483
0.8364	Intermediate Similarity	NPC44899
0.8364	Intermediate Similarity	NPC292467
0.8364	Intermediate Similarity	NPC470897
0.8351	Intermediate Similarity	NPC472811
0.835	Intermediate Similarity	NPC476764
0.835	Intermediate Similarity	NPC476763
0.8349	Intermediate Similarity	NPC203862
0.8349	Intermediate Similarity	NPC474483
0.8349	Intermediate Similarity	NPC290693
0.8333	Intermediate Similarity	NPC472815
0.8317	Intermediate Similarity	NPC476767
0.8302	Intermediate Similarity	NPC177047
0.83	Intermediate Similarity	NPC96597
0.83	Intermediate Similarity	NPC155319
0.83	Intermediate Similarity	NPC91197
0.83	Intermediate Similarity	NPC125551
0.83	Intermediate Similarity	NPC98112
0.83	Intermediate Similarity	NPC239547
0.83	Intermediate Similarity	NPC309503
0.8298	Intermediate Similarity	NPC473251
0.8298	Intermediate Similarity	NPC42586
0.8288	Intermediate Similarity	NPC470312
0.8288	Intermediate Similarity	NPC475629
0.8288	Intermediate Similarity	NPC72260
0.8288	Intermediate Similarity	NPC475136
0.8288	Intermediate Similarity	NPC475556
0.8288	Intermediate Similarity	NPC474466
0.8286	Intermediate Similarity	NPC325054
0.8286	Intermediate Similarity	NPC38948
0.8286	Intermediate Similarity	NPC470024
0.8283	Intermediate Similarity	NPC472441
0.828	Intermediate Similarity	NPC311070
0.8269	Intermediate Similarity	NPC239961
0.8269	Intermediate Similarity	NPC82251
0.8257	Intermediate Similarity	NPC207637
0.8247	Intermediate Similarity	NPC78973
0.8241	Intermediate Similarity	NPC264153
0.8235	Intermediate Similarity	NPC280991
0.8235	Intermediate Similarity	NPC471075
0.8214	Intermediate Similarity	NPC231518
0.8214	Intermediate Similarity	NPC173555
0.8214	Intermediate Similarity	NPC475590
0.8214	Intermediate Similarity	NPC120390
0.8214	Intermediate Similarity	NPC474908
0.8214	Intermediate Similarity	NPC475419
0.8214	Intermediate Similarity	NPC314535
0.8214	Intermediate Similarity	NPC475219
0.8208	Intermediate Similarity	NPC31522
0.82	Intermediate Similarity	NPC8954
0.82	Intermediate Similarity	NPC94905
0.8198	Intermediate Similarity	NPC470914
0.8198	Intermediate Similarity	NPC153085
0.8198	Intermediate Similarity	NPC268326
0.819	Intermediate Similarity	NPC475074
0.819	Intermediate Similarity	NPC109376
0.8182	Intermediate Similarity	NPC105490
0.8182	Intermediate Similarity	NPC470255
0.8173	Intermediate Similarity	NPC470768
0.8163	Intermediate Similarity	NPC477122
0.8155	Intermediate Similarity	NPC475038
0.8155	Intermediate Similarity	NPC109195
0.8155	Intermediate Similarity	NPC476769
0.8148	Intermediate Similarity	NPC473125
0.8142	Intermediate Similarity	NPC264336
0.8142	Intermediate Similarity	NPC74259
0.8142	Intermediate Similarity	NPC474423
0.8142	Intermediate Similarity	NPC193893
0.8142	Intermediate Similarity	NPC115349
0.8137	Intermediate Similarity	NPC477720
0.8137	Intermediate Similarity	NPC251680
0.8125	Intermediate Similarity	NPC476127
0.8125	Intermediate Similarity	NPC476150
0.8125	Intermediate Similarity	NPC135369
0.8119	Intermediate Similarity	NPC475709
0.8119	Intermediate Similarity	NPC97867
0.8113	Intermediate Similarity	NPC224660
0.8113	Intermediate Similarity	NPC90946
0.8113	Intermediate Similarity	NPC300614
0.8108	Intermediate Similarity	NPC218093
0.8108	Intermediate Similarity	NPC470515
0.8105	Intermediate Similarity	NPC472442
0.81	Intermediate Similarity	NPC477969
0.81	Intermediate Similarity	NPC477970
0.81	Intermediate Similarity	NPC276110
0.81	Intermediate Similarity	NPC100892
0.81	Intermediate Similarity	NPC135224
0.8095	Intermediate Similarity	NPC472818
0.8095	Intermediate Similarity	NPC473199
0.8095	Intermediate Similarity	NPC172867
0.8085	Intermediate Similarity	NPC42476
0.8085	Intermediate Similarity	NPC472440
0.8081	Intermediate Similarity	NPC474835
0.8081	Intermediate Similarity	NPC7349
0.8081	Intermediate Similarity	NPC472641
0.8081	Intermediate Similarity	NPC472640
0.8077	Intermediate Similarity	NPC10232
0.8077	Intermediate Similarity	NPC127933
0.8077	Intermediate Similarity	NPC475889
0.8077	Intermediate Similarity	NPC187302
0.8077	Intermediate Similarity	NPC473123
0.8077	Intermediate Similarity	NPC473124
0.8077	Intermediate Similarity	NPC7644
0.8077	Intermediate Similarity	NPC189588
0.8077	Intermediate Similarity	NPC196471
0.8077	Intermediate Similarity	NPC97487
0.8077	Intermediate Similarity	NPC7613
0.8073	Intermediate Similarity	NPC290608
0.8073	Intermediate Similarity	NPC44298
0.8073	Intermediate Similarity	NPC473128

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 NPC477717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1626
0.2-0.3	3979
0.3-0.4	2288
0.4-0.5	644
0.5-0.6	307
0.6-0.7	97
0.7-0.8	17
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8641	High Similarity	NPD6686	Approved
0.844	Intermediate Similarity	NPD7327	Approved
0.844	Intermediate Similarity	NPD7328	Approved
0.8364	Intermediate Similarity	NPD7516	Approved
0.8288	Intermediate Similarity	NPD8377	Approved
0.8288	Intermediate Similarity	NPD8294	Approved
0.8214	Intermediate Similarity	NPD8378	Approved
0.8214	Intermediate Similarity	NPD8380	Approved
0.8214	Intermediate Similarity	NPD8296	Approved
0.8214	Intermediate Similarity	NPD8379	Approved
0.8214	Intermediate Similarity	NPD8033	Approved
0.8214	Intermediate Similarity	NPD8335	Approved
0.8137	Intermediate Similarity	NPD7640	Approved
0.8137	Intermediate Similarity	NPD7639	Approved
0.8039	Intermediate Similarity	NPD7638	Approved
0.7931	Intermediate Similarity	NPD7507	Approved
0.7895	Intermediate Similarity	NPD7503	Approved
0.7812	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD7319	Approved
0.7685	Intermediate Similarity	NPD6412	Phase 2
0.7477	Intermediate Similarity	NPD7632	Discontinued
0.7434	Intermediate Similarity	NPD8133	Approved
0.7196	Intermediate Similarity	NPD4225	Approved
0.7167	Intermediate Similarity	NPD8328	Phase 3
0.708	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7748	Approved
0.6952	Remote Similarity	NPD7515	Phase 2
0.6952	Remote Similarity	NPD7637	Suspended
0.693	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6051	Approved
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6698	Approved
0.6857	Remote Similarity	NPD46	Approved
0.6832	Remote Similarity	NPD6695	Phase 3
0.6827	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7115	Discovery
0.6807	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7736	Approved
0.6789	Remote Similarity	NPD7902	Approved
0.6789	Remote Similarity	NPD6084	Phase 2
0.6789	Remote Similarity	NPD6083	Phase 2
0.6768	Remote Similarity	NPD7645	Phase 2
0.6765	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5344	Discontinued
0.6752	Remote Similarity	NPD6882	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8513	Phase 3
0.6698	Remote Similarity	NPD7838	Discovery
0.6691	Remote Similarity	NPD7625	Phase 1
0.6635	Remote Similarity	NPD5330	Approved
0.6635	Remote Similarity	NPD6409	Approved
0.6635	Remote Similarity	NPD6684	Approved
0.6635	Remote Similarity	NPD7521	Approved
0.6635	Remote Similarity	NPD7146	Approved
0.6635	Remote Similarity	NPD7334	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6929	Approved
0.6587	Remote Similarity	NPD8293	Discontinued
0.6574	Remote Similarity	NPD6399	Phase 3
0.6571	Remote Similarity	NPD7750	Discontinued
0.6571	Remote Similarity	NPD7524	Approved
0.6535	Remote Similarity	NPD6930	Phase 2
0.6535	Remote Similarity	NPD7525	Registered
0.6535	Remote Similarity	NPD6931	Approved
0.6532	Remote Similarity	NPD6370	Approved
0.6522	Remote Similarity	NPD6675	Approved
0.6522	Remote Similarity	NPD6402	Approved
0.6522	Remote Similarity	NPD5739	Approved
0.6522	Remote Similarity	NPD7128	Approved
0.6518	Remote Similarity	NPD6648	Approved
0.6514	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7900	Approved
0.6509	Remote Similarity	NPD6672	Approved
0.6509	Remote Similarity	NPD6903	Approved
0.6509	Remote Similarity	NPD5737	Approved
0.6496	Remote Similarity	NPD6372	Approved
0.6496	Remote Similarity	NPD6373	Approved
0.6455	Remote Similarity	NPD5695	Phase 3
0.6442	Remote Similarity	NPD3666	Approved
0.6442	Remote Similarity	NPD3133	Approved
0.6442	Remote Similarity	NPD3665	Phase 1
0.6434	Remote Similarity	NPD6914	Discontinued
0.6429	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD7492	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.6422	Remote Similarity	NPD5779	Approved
0.6415	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD6899	Approved
0.641	Remote Similarity	NPD7320	Approved
0.64	Remote Similarity	NPD6925	Approved
0.64	Remote Similarity	NPD5776	Phase 2
0.6393	Remote Similarity	NPD6009	Approved
0.6387	Remote Similarity	NPD6650	Approved
0.6387	Remote Similarity	NPD6649	Approved
0.6381	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6616	Approved
0.6373	Remote Similarity	NPD7514	Phase 3
0.6373	Remote Similarity	NPD7332	Phase 2
0.6371	Remote Similarity	NPD6059	Approved
0.6371	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD7339	Approved
0.6364	Remote Similarity	NPD6942	Approved
0.6349	Remote Similarity	NPD6067	Discontinued
0.6337	Remote Similarity	NPD7145	Approved
0.6333	Remote Similarity	NPD8297	Approved
0.633	Remote Similarity	NPD8035	Phase 2
0.633	Remote Similarity	NPD5693	Phase 1
0.633	Remote Similarity	NPD7087	Discontinued
0.633	Remote Similarity	NPD8034	Phase 2
0.633	Remote Similarity	NPD6411	Approved
0.6328	Remote Similarity	NPD7078	Approved
0.6325	Remote Similarity	NPD5701	Approved
0.6325	Remote Similarity	NPD5697	Approved
0.6321	Remote Similarity	NPD3618	Phase 1
0.6311	Remote Similarity	NPD6902	Approved
0.6303	Remote Similarity	NPD6371	Approved
0.6303	Remote Similarity	NPD7290	Approved
0.6303	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD6883	Approved
0.63	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4753	Phase 2
0.6296	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5328	Approved
0.6286	Remote Similarity	NPD4786	Approved
0.6273	Remote Similarity	NPD8171	Discontinued
0.6271	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD7839	Suspended
0.624	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD5785	Approved
0.6226	Remote Similarity	NPD6893	Approved
0.6226	Remote Similarity	NPD1694	Approved
0.6218	Remote Similarity	NPD6013	Approved
0.6218	Remote Similarity	NPD6014	Approved
0.6218	Remote Similarity	NPD6012	Approved
0.6214	Remote Similarity	NPD6928	Phase 2
0.619	Remote Similarity	NPD6016	Approved
0.619	Remote Similarity	NPD6015	Approved
0.6182	Remote Similarity	NPD6079	Approved
0.6168	Remote Similarity	NPD4623	Approved
0.6168	Remote Similarity	NPD4519	Discontinued
0.6154	Remote Similarity	NPD6898	Phase 1
0.6148	Remote Similarity	NPD4632	Approved
0.6147	Remote Similarity	NPD6080	Approved
0.6147	Remote Similarity	NPD6904	Approved
0.6147	Remote Similarity	NPD6101	Approved
0.6147	Remote Similarity	NPD6673	Approved
0.6147	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5988	Approved
0.6134	Remote Similarity	NPD6011	Approved
0.6121	Remote Similarity	NPD5211	Phase 2
0.6117	Remote Similarity	NPD4195	Approved
0.6116	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4250	Approved
0.6111	Remote Similarity	NPD3573	Approved
0.6111	Remote Similarity	NPD4251	Approved
0.6102	Remote Similarity	NPD6008	Approved
0.61	Remote Similarity	NPD6926	Approved
0.61	Remote Similarity	NPD6924	Approved
0.6078	Remote Similarity	NPD6932	Approved
0.6077	Remote Similarity	NPD8074	Phase 3
0.6075	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4755	Approved
0.605	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7154	Phase 3
0.6036	Remote Similarity	NPD7983	Approved
0.6019	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD4249	Approved
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5210	Approved
0.6018	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4629	Approved
0.6018	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5141	Approved
0.6017	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD7260	Phase 2
0.5984	Remote Similarity	NPD7741	Discontinued
0.5982	Remote Similarity	NPD4202	Approved
0.598	Remote Similarity	NPD6933	Approved
0.597	Remote Similarity	NPD8449	Approved
0.5969	Remote Similarity	NPD7604	Phase 2
0.5969	Remote Similarity	NPD7830	Approved
0.5969	Remote Similarity	NPD7829	Approved
0.5966	Remote Similarity	NPD4211	Phase 1
0.5966	Remote Similarity	NPD6640	Phase 3
0.5965	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5221	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