NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	393.521
LogP:	2.448
LogD:	2.85
LogS:	-3.559
# Rotatable Bonds:	2
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.561
Synthetic Accessibility Score:	6.317
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.802
MDCK Permeability:	8.76863778103143e-05
Pgp-inhibitor:	0.88
Pgp-substrate:	0.168
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	80.52503204345703%
Volume Distribution (VD):	2.109
Pgp-substrate:	11.698335647583008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.394
CYP3A4-inhibitor:	0.342
CYP3A4-substrate:	0.59

ADMET: Excretion

Clearance (CL):	4.611
Half-life (T1/2):	0.638

ADMET: Toxicity

hERG Blockers:	0.203
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.82
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.139
Carcinogencity:	0.032
Eye Corrosion:	0.005
Eye Irritation:	0.015
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC476720

Natural Product ID:	NPC476720
*Common Name:**	[(2S,3R,4R,5R,8R,11S,14R,15Z)-14-hydroxy-5,8,11,15-tetramethyl-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadec-15-en-4-yl] acetate
IUPAC Name:	[(2S,3R,4R,5R,8R,11S,14R,15Z)-14-hydroxy-5,8,11,15-tetramethyl-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadec-15-en-4-yl] acetate
Synonyms:	Asbestinin-26
Standard InCHIKey:	QQUBMUOPSYDXCO-WRHDSNLJSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-11-9-17-19-18-15(8-12(2)20(19)26-14(4)23)13(3)10-25-22(5,21(18)27-17)7-6-16(11)24/h9,12-13,15-21,24H,6-8,10H2,1-5H3/b11-9-/t12-,13+,15?,16-,17?,18+,19+,20-,21?,22+/m1/s1
SMILES:	C[C@@H]1CC2[C@H](CO[C@]3(CC[C@H](/C(=C\C4[C@H]([C@@H]1OC(=O)C)[C@H]2C3O4)/C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566429
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO33599	Briareum polyanthes	Species	Briareidae	Eukaryota	n.a.	coral reef off Cabo Rojo, Puerto Rico, at a depth of 10-15 m	2000-OCT	PMID[17190449]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	18	ug/ml	PMID[17190449]

☑ 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 NPC476720 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	173
0.1-0.2	1313
0.2-0.3	4528
0.3-0.4	10644
0.4-0.5	12279
0.5-0.6	7231
0.6-0.7	5636
0.7-0.8	861
0.8-0.85	26
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9149	High Similarity	NPC272223
0.8889	High Similarity	NPC476723
0.8889	High Similarity	NPC476724
0.8876	High Similarity	NPC214315
0.8667	High Similarity	NPC475684
0.8571	High Similarity	NPC44538
0.8542	High Similarity	NPC473244
0.8478	Intermediate Similarity	NPC92370
0.8478	Intermediate Similarity	NPC470260
0.8478	Intermediate Similarity	NPC75443
0.8387	Intermediate Similarity	NPC161560
0.8387	Intermediate Similarity	NPC246028
0.8387	Intermediate Similarity	NPC291875
0.837	Intermediate Similarity	NPC166857
0.8367	Intermediate Similarity	NPC38855
0.8352	Intermediate Similarity	NPC471379
0.8352	Intermediate Similarity	NPC476725
0.8352	Intermediate Similarity	NPC196911
0.8333	Intermediate Similarity	NPC127917
0.8333	Intermediate Similarity	NPC5958
0.83	Intermediate Similarity	NPC473523
0.8298	Intermediate Similarity	NPC209816
0.8247	Intermediate Similarity	NPC284194
0.8247	Intermediate Similarity	NPC211810
0.8247	Intermediate Similarity	NPC471765
0.8247	Intermediate Similarity	NPC221801
0.8229	Intermediate Similarity	NPC472360
0.8229	Intermediate Similarity	NPC476716
0.8229	Intermediate Similarity	NPC105490
0.8229	Intermediate Similarity	NPC472416
0.8218	Intermediate Similarity	NPC473543
0.8211	Intermediate Similarity	NPC122057
0.8211	Intermediate Similarity	NPC249034
0.8211	Intermediate Similarity	NPC91251
0.8211	Intermediate Similarity	NPC8729
0.8163	Intermediate Similarity	NPC254121
0.8155	Intermediate Similarity	NPC38948
0.8144	Intermediate Similarity	NPC276110
0.8125	Intermediate Similarity	NPC7349
0.8111	Intermediate Similarity	NPC77003
0.8105	Intermediate Similarity	NPC471378
0.8105	Intermediate Similarity	NPC312471
0.8105	Intermediate Similarity	NPC220216
0.81	Intermediate Similarity	NPC472554
0.81	Intermediate Similarity	NPC475617
0.81	Intermediate Similarity	NPC11974
0.8085	Intermediate Similarity	NPC309656
0.8077	Intermediate Similarity	NPC206618
0.8061	Intermediate Similarity	NPC472995
0.8061	Intermediate Similarity	NPC475304
0.8058	Intermediate Similarity	NPC471205
0.8043	Intermediate Similarity	NPC102048
0.8039	Intermediate Similarity	NPC475585
0.8039	Intermediate Similarity	NPC474550
0.8039	Intermediate Similarity	NPC473577
0.8022	Intermediate Similarity	NPC103171
0.8021	Intermediate Similarity	NPC124374
0.8021	Intermediate Similarity	NPC473675
0.8021	Intermediate Similarity	NPC208839
0.802	Intermediate Similarity	NPC475038
0.802	Intermediate Similarity	NPC472815
0.802	Intermediate Similarity	NPC472552
0.802	Intermediate Similarity	NPC475344
0.802	Intermediate Similarity	NPC470972
0.802	Intermediate Similarity	NPC476471
0.802	Intermediate Similarity	NPC109195
0.8	Intermediate Similarity	NPC324841
0.8	Intermediate Similarity	NPC188968
0.8	Intermediate Similarity	NPC261320
0.798	Intermediate Similarity	NPC210337
0.7979	Intermediate Similarity	NPC476948
0.7961	Intermediate Similarity	NPC475290
0.7959	Intermediate Similarity	NPC86893
0.7959	Intermediate Similarity	NPC292178
0.7957	Intermediate Similarity	NPC35933
0.7941	Intermediate Similarity	NPC475623
0.7941	Intermediate Similarity	NPC474124
0.7941	Intermediate Similarity	NPC475334
0.7941	Intermediate Similarity	NPC473694
0.7938	Intermediate Similarity	NPC99653
0.7938	Intermediate Similarity	NPC53555
0.7917	Intermediate Similarity	NPC78973
0.7912	Intermediate Similarity	NPC118116
0.79	Intermediate Similarity	NPC278673
0.79	Intermediate Similarity	NPC325229
0.79	Intermediate Similarity	NPC470067
0.79	Intermediate Similarity	NPC470066
0.79	Intermediate Similarity	NPC275086
0.7885	Intermediate Similarity	NPC187435
0.7885	Intermediate Similarity	NPC67321
0.7885	Intermediate Similarity	NPC475781
0.7879	Intermediate Similarity	NPC129569
0.7879	Intermediate Similarity	NPC88009
0.7864	Intermediate Similarity	NPC121518
0.7864	Intermediate Similarity	NPC181104
0.7864	Intermediate Similarity	NPC475331
0.7864	Intermediate Similarity	NPC80809
0.7864	Intermediate Similarity	NPC288502
0.7864	Intermediate Similarity	NPC475335
0.7864	Intermediate Similarity	NPC103298
0.7864	Intermediate Similarity	NPC201144
0.7857	Intermediate Similarity	NPC96736
0.7857	Intermediate Similarity	NPC182826
0.7857	Intermediate Similarity	NPC105375
0.7857	Intermediate Similarity	NPC178949
0.7843	Intermediate Similarity	NPC238397
0.7843	Intermediate Similarity	NPC165578
0.7843	Intermediate Similarity	NPC471363
0.7843	Intermediate Similarity	NPC11956
0.7835	Intermediate Similarity	NPC312805
0.7826	Intermediate Similarity	NPC155521
0.7822	Intermediate Similarity	NPC219285
0.7822	Intermediate Similarity	NPC477968
0.7822	Intermediate Similarity	NPC477971
0.7822	Intermediate Similarity	NPC228251
0.7822	Intermediate Similarity	NPC20113
0.7822	Intermediate Similarity	NPC474718
0.7822	Intermediate Similarity	NPC161527
0.7822	Intermediate Similarity	NPC230546
0.7822	Intermediate Similarity	NPC477972
0.7822	Intermediate Similarity	NPC473510
0.7812	Intermediate Similarity	NPC115607
0.7812	Intermediate Similarity	NPC170633
0.7812	Intermediate Similarity	NPC20946
0.781	Intermediate Similarity	NPC128795
0.781	Intermediate Similarity	NPC217921
0.781	Intermediate Similarity	NPC48548
0.781	Intermediate Similarity	NPC135015
0.78	Intermediate Similarity	NPC51499
0.78	Intermediate Similarity	NPC120446
0.78	Intermediate Similarity	NPC26307
0.78	Intermediate Similarity	NPC472998
0.7789	Intermediate Similarity	NPC471796
0.7789	Intermediate Similarity	NPC131329
0.7789	Intermediate Similarity	NPC471779
0.7788	Intermediate Similarity	NPC471206
0.7788	Intermediate Similarity	NPC60315
0.7788	Intermediate Similarity	NPC470980
0.7788	Intermediate Similarity	NPC51719
0.7778	Intermediate Similarity	NPC264610
0.7767	Intermediate Similarity	NPC23584
0.7767	Intermediate Similarity	NPC475889
0.7767	Intermediate Similarity	NPC7644
0.7767	Intermediate Similarity	NPC281378
0.7767	Intermediate Similarity	NPC120009
0.7767	Intermediate Similarity	NPC134270
0.7767	Intermediate Similarity	NPC7613
0.7767	Intermediate Similarity	NPC127933
0.7757	Intermediate Similarity	NPC470076
0.7757	Intermediate Similarity	NPC475668
0.7757	Intermediate Similarity	NPC17791
0.7757	Intermediate Similarity	NPC475480
0.7757	Intermediate Similarity	NPC473921
0.7745	Intermediate Similarity	NPC96784
0.7745	Intermediate Similarity	NPC235920
0.7742	Intermediate Similarity	NPC49208
0.7742	Intermediate Similarity	NPC23748
0.7742	Intermediate Similarity	NPC239308
0.7742	Intermediate Similarity	NPC231601
0.7736	Intermediate Similarity	NPC40728
0.7736	Intermediate Similarity	NPC42662
0.7736	Intermediate Similarity	NPC316974
0.7736	Intermediate Similarity	NPC475586
0.7732	Intermediate Similarity	NPC48732
0.7714	Intermediate Similarity	NPC475074
0.7714	Intermediate Similarity	NPC122816
0.7714	Intermediate Similarity	NPC125423
0.7714	Intermediate Similarity	NPC88013
0.7708	Intermediate Similarity	NPC106332
0.77	Intermediate Similarity	NPC165632
0.77	Intermediate Similarity	NPC57664
0.7692	Intermediate Similarity	NPC201880
0.7692	Intermediate Similarity	NPC258532
0.7692	Intermediate Similarity	NPC470321
0.7692	Intermediate Similarity	NPC473207
0.7692	Intermediate Similarity	NPC264867
0.7692	Intermediate Similarity	NPC81567
0.7685	Intermediate Similarity	NPC470025
0.7685	Intermediate Similarity	NPC321272
0.7685	Intermediate Similarity	NPC328074
0.7685	Intermediate Similarity	NPC317460
0.7684	Intermediate Similarity	NPC321812
0.7684	Intermediate Similarity	NPC322922
0.7684	Intermediate Similarity	NPC131813
0.7677	Intermediate Similarity	NPC473258
0.7677	Intermediate Similarity	NPC57117
0.7677	Intermediate Similarity	NPC140277
0.7677	Intermediate Similarity	NPC474922
0.767	Intermediate Similarity	NPC478156
0.767	Intermediate Similarity	NPC474709
0.767	Intermediate Similarity	NPC476081
0.767	Intermediate Similarity	NPC470571
0.7667	Intermediate Similarity	NPC40049
0.7667	Intermediate Similarity	NPC476719
0.7664	Intermediate Similarity	NPC475134
0.7664	Intermediate Similarity	NPC475563
0.7664	Intermediate Similarity	NPC177047
0.766	Intermediate Similarity	NPC222634
0.766	Intermediate Similarity	NPC83702
0.7653	Intermediate Similarity	NPC477574

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 NPC476720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1661
0.2-0.3	3924
0.3-0.4	2310
0.4-0.5	702
0.5-0.6	292
0.6-0.7	110
0.7-0.8	6
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
0.7921	Intermediate Similarity	NPD5344	Discontinued
0.7647	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD6648	Approved
0.7647	Intermediate Similarity	NPD7639	Approved
0.7549	Intermediate Similarity	NPD4225	Approved
0.7549	Intermediate Similarity	NPD7638	Approved
0.7193	Intermediate Similarity	NPD7327	Approved
0.7193	Intermediate Similarity	NPD7328	Approved
0.713	Intermediate Similarity	NPD7516	Approved
0.7091	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8294	Approved
0.7069	Intermediate Similarity	NPD8377	Approved
0.703	Intermediate Similarity	NPD6698	Approved
0.703	Intermediate Similarity	NPD46	Approved
0.703	Intermediate Similarity	NPD7838	Discovery
0.7009	Intermediate Similarity	NPD8296	Approved
0.7009	Intermediate Similarity	NPD8335	Approved
0.7009	Intermediate Similarity	NPD8380	Approved
0.7009	Intermediate Similarity	NPD8378	Approved
0.7009	Intermediate Similarity	NPD8379	Approved
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7009	Intermediate Similarity	NPD8033	Approved
0.7	Intermediate Similarity	NPD6686	Approved
0.6903	Remote Similarity	NPD6053	Discontinued
0.6875	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7503	Approved
0.681	Remote Similarity	NPD7115	Discovery
0.6777	Remote Similarity	NPD7507	Approved
0.6768	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7524	Approved
0.6733	Remote Similarity	NPD4250	Approved
0.6733	Remote Similarity	NPD4251	Approved
0.6731	Remote Similarity	NPD5778	Approved
0.6731	Remote Similarity	NPD5779	Approved
0.6729	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6371	Approved
0.6723	Remote Similarity	NPD8517	Approved
0.6723	Remote Similarity	NPD8515	Approved
0.6723	Remote Similarity	NPD8516	Approved
0.6723	Remote Similarity	NPD8513	Phase 3
0.6701	Remote Similarity	NPD7525	Registered
0.6696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6695	Phase 3
0.6635	Remote Similarity	NPD7983	Approved
0.6635	Remote Similarity	NPD7637	Suspended
0.6634	Remote Similarity	NPD4249	Approved
0.6613	Remote Similarity	NPD7319	Approved
0.6607	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6051	Approved
0.6552	Remote Similarity	NPD8133	Approved
0.6538	Remote Similarity	NPD3168	Discontinued
0.6535	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4822	Approved
0.6531	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4821	Approved
0.6531	Remote Similarity	NPD4819	Approved
0.6531	Remote Similarity	NPD4820	Approved
0.6518	Remote Similarity	NPD6675	Approved
0.6518	Remote Similarity	NPD6402	Approved
0.6518	Remote Similarity	NPD7128	Approved
0.6518	Remote Similarity	NPD5739	Approved
0.6466	Remote Similarity	NPD8297	Approved
0.6452	Remote Similarity	NPD8074	Phase 3
0.6436	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7645	Phase 2
0.6423	Remote Similarity	NPD7492	Approved
0.6415	Remote Similarity	NPD6399	Phase 3
0.641	Remote Similarity	NPD4632	Approved
0.6408	Remote Similarity	NPD7750	Discontinued
0.6404	Remote Similarity	NPD6881	Approved
0.6404	Remote Similarity	NPD6899	Approved
0.6404	Remote Similarity	NPD7320	Approved
0.6389	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD6059	Approved
0.6364	Remote Similarity	NPD6930	Phase 2
0.6364	Remote Similarity	NPD6931	Approved
0.6364	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD6319	Approved
0.6355	Remote Similarity	NPD7748	Approved
0.6348	Remote Similarity	NPD6372	Approved
0.6348	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6373	Approved
0.6337	Remote Similarity	NPD7154	Phase 3
0.633	Remote Similarity	NPD7902	Approved
0.6327	Remote Similarity	NPD4271	Approved
0.6327	Remote Similarity	NPD4268	Approved
0.6321	Remote Similarity	NPD7515	Phase 2
0.632	Remote Similarity	NPD7078	Approved
0.632	Remote Similarity	NPD8293	Discontinued
0.6316	Remote Similarity	NPD6412	Phase 2
0.6316	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD5697	Approved
0.6293	Remote Similarity	NPD7290	Approved
0.6293	Remote Similarity	NPD7102	Approved
0.6293	Remote Similarity	NPD6883	Approved
0.6292	Remote Similarity	NPD368	Approved
0.6286	Remote Similarity	NPD1695	Approved
0.627	Remote Similarity	NPD7736	Approved
0.6263	Remote Similarity	NPD6929	Approved
0.626	Remote Similarity	NPD6370	Approved
0.625	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6238	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6008	Approved
0.6214	Remote Similarity	NPD1694	Approved
0.6214	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7604	Phase 2
0.6207	Remote Similarity	NPD6013	Approved
0.6207	Remote Similarity	NPD6014	Approved
0.6207	Remote Similarity	NPD6012	Approved
0.62	Remote Similarity	NPD7514	Phase 3
0.62	Remote Similarity	NPD7332	Phase 2
0.6186	Remote Similarity	NPD6882	Approved
0.6182	Remote Similarity	NPD6083	Phase 2
0.6182	Remote Similarity	NPD6084	Phase 2
0.6179	Remote Similarity	NPD6015	Approved
0.6179	Remote Similarity	NPD5983	Phase 2
0.6179	Remote Similarity	NPD6016	Approved
0.6176	Remote Similarity	NPD5362	Discontinued
0.6168	Remote Similarity	NPD8034	Phase 2
0.6168	Remote Similarity	NPD8035	Phase 2
0.6168	Remote Similarity	NPD7087	Discontinued
0.6147	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6101	Approved
0.6132	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5988	Approved
0.6121	Remote Similarity	NPD6011	Approved
0.6111	Remote Similarity	NPD6336	Discontinued
0.6106	Remote Similarity	NPD5211	Phase 2
0.6102	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5357	Phase 1
0.6087	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8328	Phase 3
0.6078	Remote Similarity	NPD6435	Approved
0.6061	Remote Similarity	NPD5776	Phase 2
0.6061	Remote Similarity	NPD6925	Approved
0.6058	Remote Similarity	NPD6893	Approved
0.6058	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7900	Approved
0.6048	Remote Similarity	NPD6921	Approved
0.6036	Remote Similarity	NPD4755	Approved
0.602	Remote Similarity	NPD8264	Approved
0.602	Remote Similarity	NPD6942	Approved
0.602	Remote Similarity	NPD7339	Approved
0.6019	Remote Similarity	NPD5332	Approved
0.6019	Remote Similarity	NPD5331	Approved
0.6019	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3669	Approved
0.6018	Remote Similarity	NPD4159	Approved
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD5141	Approved
0.5984	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5328	Approved
0.598	Remote Similarity	NPD4790	Discontinued
0.598	Remote Similarity	NPD6902	Approved
0.598	Remote Similarity	NPD6898	Phase 1
0.5963	Remote Similarity	NPD4202	Approved
0.5962	Remote Similarity	NPD4786	Approved
0.596	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6933	Approved
0.5952	Remote Similarity	NPD6067	Discontinued
0.5948	Remote Similarity	NPD6640	Phase 3
0.5946	Remote Similarity	NPD7839	Suspended
0.5938	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD4700	Approved
0.5929	Remote Similarity	NPD5286	Approved
0.5929	Remote Similarity	NPD5285	Approved
0.5929	Remote Similarity	NPD4696	Approved
0.5926	Remote Similarity	NPD5785	Approved
0.5922	Remote Similarity	NPD4269	Approved
0.5922	Remote Similarity	NPD4270	Approved
0.5922	Remote Similarity	NPD3667	Approved
0.5918	Remote Similarity	NPD1810	Approved
0.5918	Remote Similarity	NPD1811	Approved
0.5918	Remote Similarity	NPD6924	Approved
0.5918	Remote Similarity	NPD6926	Approved
0.5909	Remote Similarity	NPD5282	Discontinued
0.5902	Remote Similarity	NPD6274	Approved
0.59	Remote Similarity	NPD6932	Approved
0.5891	Remote Similarity	NPD6033	Approved
0.5887	Remote Similarity	NPD7101	Approved
0.5887	Remote Similarity	NPD7100	Approved
0.5882	Remote Similarity	NPD5368	Approved
0.5882	Remote Similarity	NPD4634	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data