NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	418.27
Volume:	454.612
LogP:	4.399
LogD:	4.086
LogS:	-3.849
# Rotatable Bonds:	10
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	4.464
Fsp3:	0.64
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.113
MDCK Permeability:	2.446869621053338e-05
Pgp-inhibitor:	0.147
Pgp-substrate:	0.94
Human Intestinal Absorption (HIA):	0.096
20% Bioavailability (F20%):	0.183
30% Bioavailability (F30%):	0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.274
Plasma Protein Binding (PPB):	94.9192886352539%
Volume Distribution (VD):	0.533
Pgp-substrate:	1.8282470703125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.464
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.291
CYP2C9-inhibitor:	0.401
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.226
CYP2D6-substrate:	0.665
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.109

ADMET: Excretion

Clearance (CL):	8.823
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.528
Carcinogencity:	0.166
Eye Corrosion:	0.009
Eye Irritation:	0.075
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC476487

Natural Product ID:	NPC476487
*Common Name:**	acantholide D
IUPAC Name:	3-[(3E,7E)-10-[(1S,5S)-1-acetyl-5-hydroxy-2,2-dimethylcyclopentyl]-4,8-dimethyldeca-3,7-dienyl]-2-hydroxy-2H-furan-5-one
Synonyms:	Acantholide D
Standard InCHIKey:	BDWHNXBIFYPWRV-QZKWSPDJSA-N
Standard InCHI:	InChI=1S/C25H38O5/c1-17(10-7-11-20-16-22(28)30-23(20)29)8-6-9-18(2)12-15-25(19(3)26)21(27)13-14-24(25,4)5/h9-10,16,21,23,27,29H,6-8,11-15H2,1-5H3/b17-10+,18-9+/t21-,23?,25+/m0/s1
SMILES:	C/C(=C\CCC1=CC(=O)OC1O)/CC/C=C(\C)/CC[C@]2([C@H](CCC2(C)C)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11452844
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510593]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15568767]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257533]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834155]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	>	10	ug/ml	PMID[15568767]

☑ 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 NPC476487 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	199
0.1-0.2	1223
0.2-0.3	5182
0.3-0.4	12163
0.4-0.5	11569
0.5-0.6	6862
0.6-0.7	4752
0.7-0.8	716
0.8-0.85	24
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476488
0.8636	High Similarity	NPC471296
0.8557	High Similarity	NPC469872
0.8557	High Similarity	NPC469864
0.8542	High Similarity	NPC477949
0.8352	Intermediate Similarity	NPC471300
0.8352	Intermediate Similarity	NPC474860
0.8351	Intermediate Similarity	NPC475709
0.8283	Intermediate Similarity	NPC477950
0.8105	Intermediate Similarity	NPC232426
0.8105	Intermediate Similarity	NPC477782
0.8105	Intermediate Similarity	NPC281942
0.8061	Intermediate Similarity	NPC470801
0.8041	Intermediate Similarity	NPC53685
0.8041	Intermediate Similarity	NPC96541
0.8022	Intermediate Similarity	NPC471298
0.8021	Intermediate Similarity	NPC141831
0.8021	Intermediate Similarity	NPC477783
0.798	Intermediate Similarity	NPC53844
0.7959	Intermediate Similarity	NPC469873
0.7938	Intermediate Similarity	NPC37816
0.7935	Intermediate Similarity	NPC471297
0.7921	Intermediate Similarity	NPC475099
0.7917	Intermediate Similarity	NPC51486
0.7917	Intermediate Similarity	NPC145666
0.7912	Intermediate Similarity	NPC47031
0.79	Intermediate Similarity	NPC471610
0.7879	Intermediate Similarity	NPC240673
0.7879	Intermediate Similarity	NPC17578
0.7872	Intermediate Similarity	NPC261721
0.7857	Intermediate Similarity	NPC474555
0.7857	Intermediate Similarity	NPC475572
0.7849	Intermediate Similarity	NPC471301
0.7849	Intermediate Similarity	NPC31086
0.7849	Intermediate Similarity	NPC471302
0.7835	Intermediate Similarity	NPC472814
0.7835	Intermediate Similarity	NPC177037
0.783	Intermediate Similarity	NPC179642
0.7826	Intermediate Similarity	NPC7414
0.7812	Intermediate Similarity	NPC251528
0.7789	Intermediate Similarity	NPC312561
0.7789	Intermediate Similarity	NPC475678
0.7768	Intermediate Similarity	NPC470418
0.7766	Intermediate Similarity	NPC261380
0.7766	Intermediate Similarity	NPC245434
0.7755	Intermediate Similarity	NPC115021
0.7745	Intermediate Similarity	NPC471075
0.7745	Intermediate Similarity	NPC171759
0.7732	Intermediate Similarity	NPC475879
0.7723	Intermediate Similarity	NPC141191
0.7708	Intermediate Similarity	NPC472810
0.7708	Intermediate Similarity	NPC472809
0.77	Intermediate Similarity	NPC185553
0.77	Intermediate Similarity	NPC242848
0.7692	Intermediate Similarity	NPC469690
0.7692	Intermediate Similarity	NPC469620
0.7692	Intermediate Similarity	NPC201225
0.7684	Intermediate Similarity	NPC474045
0.7684	Intermediate Similarity	NPC261253
0.7677	Intermediate Similarity	NPC90453
0.7677	Intermediate Similarity	NPC167219
0.7677	Intermediate Similarity	NPC469632
0.7677	Intermediate Similarity	NPC474554
0.7677	Intermediate Similarity	NPC65829
0.767	Intermediate Similarity	NPC25639
0.7653	Intermediate Similarity	NPC221282
0.7653	Intermediate Similarity	NPC472705
0.7647	Intermediate Similarity	NPC477720
0.7642	Intermediate Similarity	NPC220155
0.7634	Intermediate Similarity	NPC323251
0.7632	Intermediate Similarity	NPC472768
0.7629	Intermediate Similarity	NPC470734
0.7629	Intermediate Similarity	NPC477215
0.7629	Intermediate Similarity	NPC476388
0.7629	Intermediate Similarity	NPC212664
0.7629	Intermediate Similarity	NPC5509
0.7629	Intermediate Similarity	NPC170775
0.7624	Intermediate Similarity	NPC213947
0.7624	Intermediate Similarity	NPC108475
0.7624	Intermediate Similarity	NPC253826
0.7624	Intermediate Similarity	NPC476253
0.7624	Intermediate Similarity	NPC170143
0.7624	Intermediate Similarity	NPC69385
0.7624	Intermediate Similarity	NPC169205
0.7624	Intermediate Similarity	NPC475894
0.7609	Intermediate Similarity	NPC115418
0.7604	Intermediate Similarity	NPC471657
0.7604	Intermediate Similarity	NPC45957
0.76	Intermediate Similarity	NPC209355
0.7579	Intermediate Similarity	NPC11804
0.7573	Intermediate Similarity	NPC195192
0.7573	Intermediate Similarity	NPC304738
0.757	Intermediate Similarity	NPC474901
0.757	Intermediate Similarity	NPC475941
0.7556	Intermediate Similarity	NPC279537
0.7553	Intermediate Similarity	NPC472473
0.7551	Intermediate Similarity	NPC477147
0.7551	Intermediate Similarity	NPC477149
0.7551	Intermediate Similarity	NPC473448
0.7551	Intermediate Similarity	NPC77337
0.7549	Intermediate Similarity	NPC222011
0.7547	Intermediate Similarity	NPC91034
0.7544	Intermediate Similarity	NPC470419
0.7527	Intermediate Similarity	NPC325031
0.7525	Intermediate Similarity	NPC18019
0.7525	Intermediate Similarity	NPC126156
0.7525	Intermediate Similarity	NPC24956
0.7524	Intermediate Similarity	NPC309190
0.7524	Intermediate Similarity	NPC121099
0.7523	Intermediate Similarity	NPC191620
0.75	Intermediate Similarity	NPC104925
0.75	Intermediate Similarity	NPC298973
0.75	Intermediate Similarity	NPC474062
0.75	Intermediate Similarity	NPC469483
0.75	Intermediate Similarity	NPC118405
0.75	Intermediate Similarity	NPC469697
0.7477	Intermediate Similarity	NPC476765
0.7476	Intermediate Similarity	NPC472644
0.7476	Intermediate Similarity	NPC201406
0.7476	Intermediate Similarity	NPC117685
0.7476	Intermediate Similarity	NPC54705
0.7475	Intermediate Similarity	NPC472811
0.7475	Intermediate Similarity	NPC261607
0.7475	Intermediate Similarity	NPC111114
0.7475	Intermediate Similarity	NPC300312
0.7475	Intermediate Similarity	NPC290651
0.7475	Intermediate Similarity	NPC475925
0.7474	Intermediate Similarity	NPC82297
0.7474	Intermediate Similarity	NPC126518
0.7473	Intermediate Similarity	NPC473756
0.7453	Intermediate Similarity	NPC153095
0.7449	Intermediate Similarity	NPC214387
0.7449	Intermediate Similarity	NPC174342
0.7449	Intermediate Similarity	NPC232747
0.7449	Intermediate Similarity	NPC268298
0.7449	Intermediate Similarity	NPC295312
0.7447	Intermediate Similarity	NPC20262
0.7447	Intermediate Similarity	NPC85772
0.7447	Intermediate Similarity	NPC256750
0.7434	Intermediate Similarity	NPC473270
0.7431	Intermediate Similarity	NPC474750
0.7429	Intermediate Similarity	NPC112009
0.7429	Intermediate Similarity	NPC475526
0.7429	Intermediate Similarity	NPC329345
0.7429	Intermediate Similarity	NPC473283
0.7426	Intermediate Similarity	NPC37408
0.7426	Intermediate Similarity	NPC48803
0.7426	Intermediate Similarity	NPC193645
0.7426	Intermediate Similarity	NPC275960
0.7426	Intermediate Similarity	NPC90121
0.7426	Intermediate Similarity	NPC472469
0.7423	Intermediate Similarity	NPC478144
0.7423	Intermediate Similarity	NPC237540
0.7423	Intermediate Similarity	NPC201658
0.7423	Intermediate Similarity	NPC72513
0.7416	Intermediate Similarity	NPC144419
0.7407	Intermediate Similarity	NPC476759
0.7407	Intermediate Similarity	NPC47951
0.7404	Intermediate Similarity	NPC150923
0.7404	Intermediate Similarity	NPC99411
0.7404	Intermediate Similarity	NPC472643
0.74	Intermediate Similarity	NPC472812
0.74	Intermediate Similarity	NPC469692
0.74	Intermediate Similarity	NPC242069
0.74	Intermediate Similarity	NPC139692
0.74	Intermediate Similarity	NPC469645
0.74	Intermediate Similarity	NPC472303
0.74	Intermediate Similarity	NPC200237
0.7396	Intermediate Similarity	NPC65661
0.7396	Intermediate Similarity	NPC42586
0.7396	Intermediate Similarity	NPC473659
0.7396	Intermediate Similarity	NPC163606
0.7396	Intermediate Similarity	NPC86316
0.7396	Intermediate Similarity	NPC106416
0.7396	Intermediate Similarity	NPC146850
0.7396	Intermediate Similarity	NPC473251
0.7396	Intermediate Similarity	NPC125290
0.7396	Intermediate Similarity	NPC287015
0.7396	Intermediate Similarity	NPC474694
0.7396	Intermediate Similarity	NPC475860
0.7391	Intermediate Similarity	NPC128276
0.7391	Intermediate Similarity	NPC192006
0.7379	Intermediate Similarity	NPC108368
0.7379	Intermediate Similarity	NPC235464
0.7379	Intermediate Similarity	NPC166745
0.7379	Intermediate Similarity	NPC57079
0.7379	Intermediate Similarity	NPC316598
0.7379	Intermediate Similarity	NPC197386
0.7374	Intermediate Similarity	NPC71533
0.7374	Intermediate Similarity	NPC106510
0.7374	Intermediate Similarity	NPC469368
0.7374	Intermediate Similarity	NPC129419
0.7373	Intermediate Similarity	NPC311534
0.7368	Intermediate Similarity	NPC161045
0.7368	Intermediate Similarity	NPC62214
0.7368	Intermediate Similarity	NPC475947
0.7368	Intermediate Similarity	NPC193198
0.7368	Intermediate Similarity	NPC474809
0.7364	Intermediate Similarity	NPC475970
0.7363	Intermediate Similarity	NPC469646

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 NPC476487 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1839
0.2-0.3	3852
0.3-0.4	2263
0.4-0.5	564
0.5-0.6	272
0.6-0.7	156
0.7-0.8	13
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
0.8495	Intermediate Similarity	NPD5785	Approved
0.7957	Intermediate Similarity	NPD5363	Approved
0.7826	Intermediate Similarity	NPD4269	Approved
0.7826	Intermediate Similarity	NPD4270	Approved
0.7742	Intermediate Similarity	NPD5362	Discontinued
0.7684	Intermediate Similarity	NPD5786	Approved
0.7609	Intermediate Similarity	NPD4252	Approved
0.7582	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5369	Approved
0.7474	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6371	Approved
0.7315	Intermediate Similarity	NPD6686	Approved
0.7308	Intermediate Similarity	NPD7639	Approved
0.7308	Intermediate Similarity	NPD7640	Approved
0.7263	Intermediate Similarity	NPD6435	Approved
0.7234	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7638	Approved
0.7188	Intermediate Similarity	NPD7154	Phase 3
0.7188	Intermediate Similarity	NPD5332	Approved
0.7188	Intermediate Similarity	NPD5331	Approved
0.7172	Intermediate Similarity	NPD6903	Approved
0.7167	Intermediate Similarity	NPD7319	Approved
0.7158	Intermediate Similarity	NPD4790	Discontinued
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7115	Intermediate Similarity	NPD6084	Phase 2
0.7115	Intermediate Similarity	NPD6083	Phase 2
0.7083	Intermediate Similarity	NPD5209	Approved
0.7083	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6412	Phase 2
0.7064	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7507	Approved
0.7053	Intermediate Similarity	NPD4822	Approved
0.7053	Intermediate Similarity	NPD4821	Approved
0.7053	Intermediate Similarity	NPD4819	Approved
0.7053	Intermediate Similarity	NPD5368	Approved
0.7053	Intermediate Similarity	NPD4820	Approved
0.7021	Intermediate Similarity	NPD4271	Approved
0.7021	Intermediate Similarity	NPD4268	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7115	Discovery
0.6939	Remote Similarity	NPD3665	Phase 1
0.6939	Remote Similarity	NPD3666	Approved
0.6939	Remote Similarity	NPD3133	Approved
0.6923	Remote Similarity	NPD5695	Phase 3
0.69	Remote Similarity	NPD4251	Approved
0.69	Remote Similarity	NPD4250	Approved
0.6887	Remote Similarity	NPD4225	Approved
0.6847	Remote Similarity	NPD7320	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD4249	Approved
0.6796	Remote Similarity	NPD7637	Suspended
0.6796	Remote Similarity	NPD5693	Phase 1
0.6754	Remote Similarity	NPD6882	Approved
0.6754	Remote Similarity	NPD6053	Discontinued
0.6752	Remote Similarity	NPD7327	Approved
0.6752	Remote Similarity	NPD7328	Approved
0.6731	Remote Similarity	NPD6399	Phase 3
0.6731	Remote Similarity	NPD5778	Approved
0.6731	Remote Similarity	NPD5779	Approved
0.6729	Remote Similarity	NPD5696	Approved
0.6721	Remote Similarity	NPD8293	Discontinued
0.67	Remote Similarity	NPD1694	Approved
0.6699	Remote Similarity	NPD46	Approved
0.6699	Remote Similarity	NPD6698	Approved
0.6697	Remote Similarity	NPD7632	Discontinued
0.6696	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6695	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6639	Remote Similarity	NPD8377	Approved
0.6639	Remote Similarity	NPD8294	Approved
0.6637	Remote Similarity	NPD6372	Approved
0.6637	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD6411	Approved
0.6607	Remote Similarity	NPD5701	Approved
0.6607	Remote Similarity	NPD5697	Approved
0.6604	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6673	Approved
0.6602	Remote Similarity	NPD6904	Approved
0.6602	Remote Similarity	NPD5370	Suspended
0.6602	Remote Similarity	NPD4753	Phase 2
0.6602	Remote Similarity	NPD6080	Approved
0.6583	Remote Similarity	NPD8033	Approved
0.6583	Remote Similarity	NPD8296	Approved
0.6583	Remote Similarity	NPD8335	Approved
0.6583	Remote Similarity	NPD8380	Approved
0.6583	Remote Similarity	NPD8379	Approved
0.6583	Remote Similarity	NPD8378	Approved
0.6579	Remote Similarity	NPD7102	Approved
0.6579	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD6883	Approved
0.6557	Remote Similarity	NPD7492	Approved
0.6549	Remote Similarity	NPD6011	Approved
0.6542	Remote Similarity	NPD7839	Suspended
0.6526	Remote Similarity	NPD8039	Approved
0.6522	Remote Similarity	NPD6650	Approved
0.6522	Remote Similarity	NPD6617	Approved
0.6522	Remote Similarity	NPD8130	Phase 1
0.6522	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6649	Approved
0.6522	Remote Similarity	NPD6847	Approved
0.6522	Remote Similarity	NPD6869	Approved
0.6509	Remote Similarity	NPD5282	Discontinued
0.6509	Remote Similarity	NPD7748	Approved
0.6504	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD6059	Approved
0.65	Remote Similarity	NPD6054	Approved
0.6491	Remote Similarity	NPD6012	Approved
0.6491	Remote Similarity	NPD6013	Approved
0.6491	Remote Similarity	NPD6014	Approved
0.6476	Remote Similarity	NPD5281	Approved
0.6476	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6050	Approved
0.6476	Remote Similarity	NPD7983	Approved
0.6476	Remote Similarity	NPD7515	Phase 2
0.6476	Remote Similarity	NPD5284	Approved
0.6471	Remote Similarity	NPD5279	Phase 3
0.6471	Remote Similarity	NPD3618	Phase 1
0.6466	Remote Similarity	NPD8297	Approved
0.6452	Remote Similarity	NPD7078	Approved
0.6442	Remote Similarity	NPD6101	Approved
0.6442	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6051	Approved
0.6442	Remote Similarity	NPD5328	Approved
0.6436	Remote Similarity	NPD4786	Approved
0.6415	Remote Similarity	NPD4202	Approved
0.64	Remote Similarity	NPD4221	Approved
0.64	Remote Similarity	NPD4223	Phase 3
0.64	Remote Similarity	NPD3667	Approved
0.6396	Remote Similarity	NPD5211	Phase 2
0.6381	Remote Similarity	NPD5692	Phase 3
0.6381	Remote Similarity	NPD5207	Approved
0.6373	Remote Similarity	NPD5329	Approved
0.6346	Remote Similarity	NPD5208	Approved
0.6341	Remote Similarity	NPD6067	Discontinued
0.633	Remote Similarity	NPD4755	Approved
0.633	Remote Similarity	NPD7902	Approved
0.6327	Remote Similarity	NPD4238	Approved
0.6327	Remote Similarity	NPD4802	Phase 2
0.6321	Remote Similarity	NPD6079	Approved
0.6321	Remote Similarity	NPD5694	Approved
0.6311	Remote Similarity	NPD6016	Approved
0.6311	Remote Similarity	NPD7503	Approved
0.6311	Remote Similarity	NPD6098	Approved
0.6311	Remote Similarity	NPD6015	Approved
0.6311	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD4629	Approved
0.6293	Remote Similarity	NPD6420	Discontinued
0.6286	Remote Similarity	NPD1695	Approved
0.6283	Remote Similarity	NPD5141	Approved
0.6275	Remote Similarity	NPD4197	Approved
0.6273	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD6009	Approved
0.623	Remote Similarity	NPD6319	Approved
0.6228	Remote Similarity	NPD6008	Approved
0.6226	Remote Similarity	NPD7838	Discovery
0.6216	Remote Similarity	NPD4700	Approved
0.6216	Remote Similarity	NPD5286	Approved
0.6216	Remote Similarity	NPD4696	Approved
0.6216	Remote Similarity	NPD5285	Approved
0.6204	Remote Similarity	NPD6001	Approved
0.6198	Remote Similarity	NPD6335	Approved
0.6179	Remote Similarity	NPD8515	Approved
0.6179	Remote Similarity	NPD8517	Approved
0.6179	Remote Similarity	NPD8516	Approved
0.6179	Remote Similarity	NPD8513	Phase 3
0.6176	Remote Similarity	NPD4788	Approved
0.6167	Remote Similarity	NPD6274	Approved
0.6161	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD4688	Approved
0.6154	Remote Similarity	NPD4689	Approved
0.6154	Remote Similarity	NPD4693	Phase 3
0.6154	Remote Similarity	NPD5205	Approved
0.6154	Remote Similarity	NPD5280	Approved
0.6154	Remote Similarity	NPD4690	Approved
0.6154	Remote Similarity	NPD5690	Phase 2
0.6154	Remote Similarity	NPD4138	Approved
0.6154	Remote Similarity	NPD4694	Approved
0.6148	Remote Similarity	NPD7101	Approved
0.6148	Remote Similarity	NPD7100	Approved
0.6142	Remote Similarity	NPD6033	Approved
0.6134	Remote Similarity	NPD8133	Approved
0.6134	Remote Similarity	NPD4632	Approved
0.6117	Remote Similarity	NPD5766	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