NPASS Compound

Structure

NPC82297 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 5.6724 -4.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4464 -2.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8718 -2.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8769 0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4635 -2.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0722 -3.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4720 -2.9243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9531 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7459 2.0731 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 5.0637 -3.4566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8633 -2.1310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9531 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2459 1.2071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2459 1.2071 0.0000 C 0 0 1 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 3.2459 -1.2071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2459 -1.2071 0.0000 C 0 0 1 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 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6286 -2.1310 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 17 1 0 0 0 0 10 16 1 0 0 0 0 10 23 1 0 0 0 0 12 3 1 1 0 0 0 13 4 1 6 0 0 0 13 14 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 15 9 1 1 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 19 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 1 0 0 0 18 12 1 1 0 0 0 19 20 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	5.347
LogD:	4.819
LogS:	-3.846
# Rotatable Bonds:	4
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	4.883
Fsp3:	0.7
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:	-4.798
MDCK Permeability:	1.1625294064288028e-05
Pgp-inhibitor:	0.132
Pgp-substrate:	0.753
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.195
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.289
Plasma Protein Binding (PPB):	96.0630111694336%
Volume Distribution (VD):	4.306
Pgp-substrate:	3.9748165607452393%

ADMET: Metabolism

CYP1A2-inhibitor:	0.201
CYP1A2-substrate:	0.685
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.507
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.49

ADMET: Excretion

Clearance (CL):	14.394
Half-life (T1/2):	0.267

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.71
Drug-inuced Liver Injury (DILI):	0.499
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.817
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.74
Carcinogencity:	0.174
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.855

Download Data

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

Natural Product: NPC82297

Natural Product ID:	NPC82297
*Common Name:**	GPYUIWHQODGMSY-ZTNNJZCJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GPYUIWHQODGMSY-ZTNNJZCJSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-11(2)6-5-7-12(3)18-16-10-23-20(22)19(16)15-9-14(15)13(4)8-17(18)21/h6,12-15,17-18,21H,5,7-10H2,1-4H3/t12-,13-,14+,15+,17-,18+/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@H]1C2=C([C@H]3C[C@H]3[C@H](C)C[C@H]1O)C(=O)OC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3355409
PubChem CID:	158582
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO32773	dictyota plectens	Species	Dictyotaceae	Eukaryota	n.a.	China	n.a.	PMID[25495797]

☑ 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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	CC50	>	60000.0	nM	PMID[514087]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[514087]
NPT2	Others	Unspecified		Inhibition	=	62.0	%	PMID[514087]

☑ 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 NPC82297 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	203
0.1-0.2	1176
0.2-0.3	5175
0.3-0.4	13863
0.4-0.5	11082
0.5-0.6	6664
0.6-0.7	3738
0.7-0.8	772
0.8-0.85	20
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC35556
0.8659	High Similarity	NPC325031
0.8488	Intermediate Similarity	NPC312561
0.8409	Intermediate Similarity	NPC469368
0.8372	Intermediate Similarity	NPC475461
0.8372	Intermediate Similarity	NPC305475
0.8372	Intermediate Similarity	NPC261721
0.8333	Intermediate Similarity	NPC89555
0.8256	Intermediate Similarity	NPC255307
0.8202	Intermediate Similarity	NPC232426
0.8202	Intermediate Similarity	NPC473448
0.8202	Intermediate Similarity	NPC281942
0.8193	Intermediate Similarity	NPC470244
0.8193	Intermediate Similarity	NPC470239
0.8193	Intermediate Similarity	NPC89128
0.8171	Intermediate Similarity	NPC7563
0.8171	Intermediate Similarity	NPC320630
0.8171	Intermediate Similarity	NPC116177
0.8161	Intermediate Similarity	NPC150755
0.8148	Intermediate Similarity	NPC329852
0.814	Intermediate Similarity	NPC114979
0.814	Intermediate Similarity	NPC191476
0.814	Intermediate Similarity	NPC476804
0.8118	Intermediate Similarity	NPC474291
0.8111	Intermediate Similarity	NPC141831
0.809	Intermediate Similarity	NPC295312
0.8072	Intermediate Similarity	NPC108816
0.8072	Intermediate Similarity	NPC128276
0.8072	Intermediate Similarity	NPC93763
0.8046	Intermediate Similarity	NPC86316
0.8046	Intermediate Similarity	NPC106416
0.8046	Intermediate Similarity	NPC165162
0.8023	Intermediate Similarity	NPC131669
0.8023	Intermediate Similarity	NPC472377
0.8023	Intermediate Similarity	NPC473390
0.8023	Intermediate Similarity	NPC193198
0.8023	Intermediate Similarity	NPC40746
0.8023	Intermediate Similarity	NPC169575
0.8022	Intermediate Similarity	NPC475838
0.8022	Intermediate Similarity	NPC228451
0.8022	Intermediate Similarity	NPC125674
0.8	Intermediate Similarity	NPC471325
0.8	Intermediate Similarity	NPC52861
0.8	Intermediate Similarity	NPC141810
0.7978	Intermediate Similarity	NPC476805
0.7976	Intermediate Similarity	NPC617
0.7976	Intermediate Similarity	NPC178277
0.7976	Intermediate Similarity	NPC98557
0.7976	Intermediate Similarity	NPC167881
0.7955	Intermediate Similarity	NPC469483
0.7952	Intermediate Similarity	NPC57744
0.7935	Intermediate Similarity	NPC474247
0.7931	Intermediate Similarity	NPC141193
0.7931	Intermediate Similarity	NPC472326
0.7931	Intermediate Similarity	NPC96259
0.7912	Intermediate Similarity	NPC177037
0.7912	Intermediate Similarity	NPC472814
0.7907	Intermediate Similarity	NPC229825
0.7889	Intermediate Similarity	NPC5509
0.7889	Intermediate Similarity	NPC212598
0.7889	Intermediate Similarity	NPC268298
0.7875	Intermediate Similarity	NPC67183
0.7865	Intermediate Similarity	NPC160138
0.7865	Intermediate Similarity	NPC237540
0.7865	Intermediate Similarity	NPC474765
0.7857	Intermediate Similarity	NPC196653
0.7857	Intermediate Similarity	NPC299235
0.7857	Intermediate Similarity	NPC267231
0.7857	Intermediate Similarity	NPC471465
0.7849	Intermediate Similarity	NPC304886
0.7841	Intermediate Similarity	NPC261380
0.7841	Intermediate Similarity	NPC471795
0.7841	Intermediate Similarity	NPC65661
0.7841	Intermediate Similarity	NPC470755
0.7841	Intermediate Similarity	NPC78089
0.7831	Intermediate Similarity	NPC123360
0.7831	Intermediate Similarity	NPC235906
0.7831	Intermediate Similarity	NPC271070
0.7826	Intermediate Similarity	NPC115021
0.7826	Intermediate Similarity	NPC139692
0.7816	Intermediate Similarity	NPC250315
0.7816	Intermediate Similarity	NPC59097
0.7816	Intermediate Similarity	NPC53867
0.7805	Intermediate Similarity	NPC472966
0.7805	Intermediate Similarity	NPC476355
0.7802	Intermediate Similarity	NPC475855
0.7802	Intermediate Similarity	NPC51486
0.7802	Intermediate Similarity	NPC129419
0.7791	Intermediate Similarity	NPC281949
0.7791	Intermediate Similarity	NPC301477
0.7791	Intermediate Similarity	NPC25684
0.7791	Intermediate Similarity	NPC24417
0.7791	Intermediate Similarity	NPC470241
0.7791	Intermediate Similarity	NPC112868
0.7791	Intermediate Similarity	NPC42470
0.7789	Intermediate Similarity	NPC222303
0.7778	Intermediate Similarity	NPC472378
0.7778	Intermediate Similarity	NPC477302
0.7778	Intermediate Similarity	NPC476803
0.7778	Intermediate Similarity	NPC163003
0.7778	Intermediate Similarity	NPC202672
0.7766	Intermediate Similarity	NPC279621
0.7766	Intermediate Similarity	NPC230800
0.7753	Intermediate Similarity	NPC116575
0.7753	Intermediate Similarity	NPC107787
0.7753	Intermediate Similarity	NPC284902
0.775	Intermediate Similarity	NPC101622
0.7742	Intermediate Similarity	NPC474035
0.7742	Intermediate Similarity	NPC53685
0.7742	Intermediate Similarity	NPC81386
0.7742	Intermediate Similarity	NPC477131
0.7738	Intermediate Similarity	NPC470240
0.7738	Intermediate Similarity	NPC476794
0.7738	Intermediate Similarity	NPC65603
0.7738	Intermediate Similarity	NPC187568
0.7738	Intermediate Similarity	NPC41780
0.7727	Intermediate Similarity	NPC31086
0.7727	Intermediate Similarity	NPC165287
0.7727	Intermediate Similarity	NPC474776
0.7727	Intermediate Similarity	NPC158756
0.7722	Intermediate Similarity	NPC472266
0.7717	Intermediate Similarity	NPC219874
0.7717	Intermediate Similarity	NPC475925
0.7717	Intermediate Similarity	NPC30515
0.7701	Intermediate Similarity	NPC173609
0.7692	Intermediate Similarity	NPC218927
0.7692	Intermediate Similarity	NPC212664
0.7692	Intermediate Similarity	NPC206001
0.7692	Intermediate Similarity	NPC115179
0.7692	Intermediate Similarity	NPC106040
0.7692	Intermediate Similarity	NPC174342
0.7692	Intermediate Similarity	NPC477215
0.7692	Intermediate Similarity	NPC476388
0.7684	Intermediate Similarity	NPC69385
0.7684	Intermediate Similarity	NPC477949
0.7667	Intermediate Similarity	NPC475703
0.7667	Intermediate Similarity	NPC45957
0.7667	Intermediate Similarity	NPC471657
0.766	Intermediate Similarity	NPC471141
0.766	Intermediate Similarity	NPC14961
0.766	Intermediate Similarity	NPC209355
0.766	Intermediate Similarity	NPC270013
0.7654	Intermediate Similarity	NPC4299
0.7647	Intermediate Similarity	NPC192006
0.7647	Intermediate Similarity	NPC471220
0.7647	Intermediate Similarity	NPC474341
0.764	Intermediate Similarity	NPC474547
0.764	Intermediate Similarity	NPC215364
0.7634	Intermediate Similarity	NPC469692
0.7634	Intermediate Similarity	NPC179746
0.7634	Intermediate Similarity	NPC212486
0.7634	Intermediate Similarity	NPC81419
0.7634	Intermediate Similarity	NPC469645
0.7634	Intermediate Similarity	NPC475302
0.7634	Intermediate Similarity	NPC476049
0.7634	Intermediate Similarity	NPC475912
0.7625	Intermediate Similarity	NPC218477
0.7625	Intermediate Similarity	NPC276290
0.7619	Intermediate Similarity	NPC61863
0.7614	Intermediate Similarity	NPC52609
0.7614	Intermediate Similarity	NPC272814
0.7614	Intermediate Similarity	NPC1761
0.7614	Intermediate Similarity	NPC311070
0.7614	Intermediate Similarity	NPC474703
0.7609	Intermediate Similarity	NPC476004
0.7609	Intermediate Similarity	NPC179394
0.7609	Intermediate Similarity	NPC51004
0.7609	Intermediate Similarity	NPC144133
0.7609	Intermediate Similarity	NPC474761
0.7609	Intermediate Similarity	NPC477782
0.7604	Intermediate Similarity	NPC473326
0.7604	Intermediate Similarity	NPC141191
0.7604	Intermediate Similarity	NPC222011
0.7604	Intermediate Similarity	NPC98868
0.7604	Intermediate Similarity	NPC471610
0.759	Intermediate Similarity	NPC474758
0.759	Intermediate Similarity	NPC259599
0.759	Intermediate Similarity	NPC117746
0.759	Intermediate Similarity	NPC15499
0.759	Intermediate Similarity	NPC140287
0.759	Intermediate Similarity	NPC294434
0.7582	Intermediate Similarity	NPC475819
0.7582	Intermediate Similarity	NPC136879
0.7582	Intermediate Similarity	NPC475902
0.7579	Intermediate Similarity	NPC476315
0.7579	Intermediate Similarity	NPC242848
0.7579	Intermediate Similarity	NPC134072
0.7579	Intermediate Similarity	NPC234993
0.7561	Intermediate Similarity	NPC129665
0.7561	Intermediate Similarity	NPC472254
0.7558	Intermediate Similarity	NPC469617
0.7558	Intermediate Similarity	NPC469690
0.7558	Intermediate Similarity	NPC270126
0.7558	Intermediate Similarity	NPC182550
0.7556	Intermediate Similarity	NPC261253
0.7556	Intermediate Similarity	NPC122502
0.7556	Intermediate Similarity	NPC50637
0.7556	Intermediate Similarity	NPC474045
0.7556	Intermediate Similarity	NPC469910
0.7553	Intermediate Similarity	NPC469632

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 NPC82297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1798
0.2-0.3	3782
0.3-0.4	2302
0.4-0.5	708
0.5-0.6	293
0.6-0.7	64
0.7-0.8	9
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
0.7802	Intermediate Similarity	NPD6698	Approved
0.7802	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5785	Approved
0.7416	Intermediate Similarity	NPD7154	Phase 3
0.7416	Intermediate Similarity	NPD5362	Discontinued
0.7273	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5363	Approved
0.725	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7838	Discovery
0.7212	Intermediate Similarity	NPD6371	Approved
0.7128	Intermediate Similarity	NPD1695	Approved
0.7111	Intermediate Similarity	NPD6435	Approved
0.7111	Intermediate Similarity	NPD4270	Approved
0.7111	Intermediate Similarity	NPD4269	Approved
0.7111	Intermediate Similarity	NPD5209	Approved
0.7079	Intermediate Similarity	NPD4822	Approved
0.7079	Intermediate Similarity	NPD4821	Approved
0.7079	Intermediate Similarity	NPD4820	Approved
0.7079	Intermediate Similarity	NPD4819	Approved
0.7065	Intermediate Similarity	NPD1694	Approved
0.7045	Intermediate Similarity	NPD4271	Approved
0.7045	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4268	Approved
0.7019	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD5369	Approved
0.6989	Remote Similarity	NPD5786	Approved
0.6923	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5779	Approved
0.6907	Remote Similarity	NPD5778	Approved
0.69	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD7638	Approved
0.6889	Remote Similarity	NPD4252	Approved
0.6889	Remote Similarity	NPD5368	Approved
0.6882	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5331	Approved
0.6848	Remote Similarity	NPD5332	Approved
0.6832	Remote Similarity	NPD7640	Approved
0.6832	Remote Similarity	NPD7639	Approved
0.6813	Remote Similarity	NPD4790	Discontinued
0.6809	Remote Similarity	NPD4249	Approved
0.6804	Remote Similarity	NPD7983	Approved
0.6774	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6101	Approved
0.6759	Remote Similarity	NPD6053	Discontinued
0.6737	Remote Similarity	NPD4250	Approved
0.6737	Remote Similarity	NPD4251	Approved
0.6735	Remote Similarity	NPD6399	Phase 3
0.6705	Remote Similarity	NPD8039	Approved
0.6636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6411	Approved
0.6632	Remote Similarity	NPD5330	Approved
0.6632	Remote Similarity	NPD6684	Approved
0.6632	Remote Similarity	NPD7334	Approved
0.6632	Remote Similarity	NPD7146	Approved
0.6632	Remote Similarity	NPD6409	Approved
0.6632	Remote Similarity	NPD7521	Approved
0.6602	Remote Similarity	NPD5344	Discontinued
0.6596	Remote Similarity	NPD3666	Approved
0.6596	Remote Similarity	NPD3133	Approved
0.6596	Remote Similarity	NPD3665	Phase 1
0.6569	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3667	Approved
0.6518	Remote Similarity	NPD7115	Discovery
0.65	Remote Similarity	NPD7748	Approved
0.65	Remote Similarity	NPD5282	Discontinued
0.6495	Remote Similarity	NPD6903	Approved
0.6495	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD7902	Approved
0.6465	Remote Similarity	NPD7515	Phase 2
0.6458	Remote Similarity	NPD3618	Phase 1
0.6458	Remote Similarity	NPD5279	Phase 3
0.6436	Remote Similarity	NPD5695	Phase 3
0.6422	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4786	Approved
0.6374	Remote Similarity	NPD4756	Discovery
0.6373	Remote Similarity	NPD7839	Suspended
0.6364	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6675	Approved
0.6355	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6402	Approved
0.6355	Remote Similarity	NPD5739	Approved
0.6353	Remote Similarity	NPD7331	Phase 2
0.6346	Remote Similarity	NPD6648	Approved
0.6327	Remote Similarity	NPD6672	Approved
0.6327	Remote Similarity	NPD5737	Approved
0.631	Remote Similarity	NPD3197	Phase 1
0.63	Remote Similarity	NPD5693	Phase 1
0.63	Remote Similarity	NPD7637	Suspended
0.6296	Remote Similarity	NPD5701	Approved
0.6296	Remote Similarity	NPD5697	Approved
0.6263	Remote Similarity	NPD5370	Suspended
0.6263	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD6011	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6239	Remote Similarity	NPD7320	Approved
0.6238	Remote Similarity	NPD4202	Approved
0.6235	Remote Similarity	NPD7341	Phase 2
0.6226	Remote Similarity	NPD7632	Discontinued
0.6186	Remote Similarity	NPD1696	Phase 3
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6013	Approved
0.6182	Remote Similarity	NPD6014	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6182	Remote Similarity	NPD6012	Approved
0.6176	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7900	Approved
0.617	Remote Similarity	NPD4695	Discontinued
0.6147	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6079	Approved
0.6139	Remote Similarity	NPD5284	Approved
0.6139	Remote Similarity	NPD5281	Approved
0.6139	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD4623	Approved
0.6122	Remote Similarity	NPD4519	Discontinued
0.6122	Remote Similarity	NPD6422	Discontinued
0.6117	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4753	Phase 2
0.6083	Remote Similarity	NPD7507	Approved
0.6076	Remote Similarity	NPD3172	Approved
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD6650	Approved
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6649	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6071	Remote Similarity	NPD368	Approved
0.6055	Remote Similarity	NPD6008	Approved
0.6042	Remote Similarity	NPD4221	Approved
0.6042	Remote Similarity	NPD4223	Phase 3
0.6024	Remote Similarity	NPD3198	Approved
0.602	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6001	Approved
0.6019	Remote Similarity	NPD6647	Phase 2
0.6018	Remote Similarity	NPD8297	Approved
0.6018	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD4266	Approved
0.6	Remote Similarity	NPD3194	Approved
0.6	Remote Similarity	NPD3196	Approved
0.6	Remote Similarity	NPD3195	Phase 2
0.6	Remote Similarity	NPD4755	Approved
0.5982	Remote Similarity	NPD2067	Discontinued
0.5982	Remote Similarity	NPD6420	Discontinued
0.598	Remote Similarity	NPD8034	Phase 2
0.598	Remote Similarity	NPD8035	Phase 2
0.5977	Remote Similarity	NPD3704	Approved
0.5941	Remote Similarity	NPD6904	Approved
0.5941	Remote Similarity	NPD6080	Approved
0.5941	Remote Similarity	NPD6673	Approved
0.5941	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6051	Approved
0.5938	Remote Similarity	NPD857	Phase 3
0.5935	Remote Similarity	NPD7319	Approved
0.5926	Remote Similarity	NPD5211	Phase 2
0.5918	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4197	Approved
0.5918	Remote Similarity	NPD3668	Phase 3
0.5909	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5221	Approved
0.5905	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4697	Phase 3
0.5905	Remote Similarity	NPD5222	Approved
0.59	Remote Similarity	NPD3573	Approved
0.5888	Remote Similarity	NPD4700	Approved
0.5888	Remote Similarity	NPD5285	Approved
0.5888	Remote Similarity	NPD5286	Approved
0.5888	Remote Similarity	NPD4696	Approved
0.5882	Remote Similarity	NPD5692	Phase 3
0.5882	Remote Similarity	NPD8517	Approved
0.5882	Remote Similarity	NPD8515	Approved
0.5882	Remote Similarity	NPD8516	Approved
0.5882	Remote Similarity	NPD5207	Approved
0.5882	Remote Similarity	NPD8513	Phase 3
0.5876	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6926	Approved
0.587	Remote Similarity	NPD6924	Approved
0.5862	Remote Similarity	NPD6274	Approved
0.5859	Remote Similarity	NPD5329	Approved
0.5849	Remote Similarity	NPD5173	Approved
0.5842	Remote Similarity	NPD4518	Approved
0.5833	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5223	Approved
0.5826	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD6050	Approved
0.5825	Remote Similarity	NPD5694	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