NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.12
Volume:	266.993
LogP:	2.869
LogD:	2.348
LogS:	-2.158
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	3.732
Fsp3:	0.5
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:	-4.786
MDCK Permeability:	1.757467725838069e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.529
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.692
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	83.66474151611328%
Volume Distribution (VD):	1.339
Pgp-substrate:	16.560195922851562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.172
CYP2C19-inhibitor:	0.27
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.347
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.792
CYP2D6-substrate:	0.349
CYP3A4-inhibitor:	0.49
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	13.68
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.271
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.778
Carcinogencity:	0.147
Eye Corrosion:	0.061
Eye Irritation:	0.889
Respiratory Toxicity:	0.476

Download Data

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

Natural Product: NPC105456

Natural Product ID:	NPC105456
*Common Name:**	3R,5S-Sonnerlactone
IUPAC Name:	(3R,5S)-5,10,12-trihydroxy-3-methyl-3,4,5,6,7,8-hexahydro-2-benzoxecin-1-one
Synonyms:	3R,5S-Sonnerlactone
Standard InCHIKey:	MQAGIKOTEWULFX-SCZZXKLOSA-N
Standard InCHI:	InChI=1S/C14H18O5/c1-8-5-10(15)4-2-3-9-6-11(16)7-12(17)13(9)14(18)19-8/h6-8,10,15-17H,2-5H2,1H3/t8-,10+/m1/s1
SMILES:	C[C@@H]1C[C@H](CCCc2cc(cc(c2C(=O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1084896
PubChem CID:	46890202
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO33319	zh6-b1	n.a.	n.a.	n.a.	n.a.	South China Sea	n.a.	PMID[20452765]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	41.6	%	PMID[505105]

☑ 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 NPC105456 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	306
0.1-0.2	1311
0.2-0.3	3366
0.3-0.4	7575
0.4-0.5	11181
0.5-0.6	3995
0.6-0.7	6882
0.7-0.8	6681
0.8-0.85	1067
0.85-0.9	221
0.9-0.95	89
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC139634
0.9774	High Similarity	NPC212693
0.9774	High Similarity	NPC94248
0.9699	High Similarity	NPC70380
0.9627	High Similarity	NPC191835
0.9556	High Similarity	NPC32360
0.9556	High Similarity	NPC474655
0.9545	High Similarity	NPC153783
0.9485	High Similarity	NPC158472
0.9481	High Similarity	NPC478200
0.9481	High Similarity	NPC33144
0.9481	High Similarity	NPC472602
0.9478	High Similarity	NPC235115
0.942	High Similarity	NPC51106
0.942	High Similarity	NPC469542
0.9416	High Similarity	NPC313123
0.9416	High Similarity	NPC478217
0.9416	High Similarity	NPC1704
0.9416	High Similarity	NPC472604
0.9416	High Similarity	NPC158634
0.9416	High Similarity	NPC244923
0.9416	High Similarity	NPC472605
0.9416	High Similarity	NPC67650
0.9416	High Similarity	NPC53649
0.9412	High Similarity	NPC268052
0.9407	High Similarity	NPC71256
0.9394	High Similarity	NPC219892
0.9394	High Similarity	NPC189823
0.9348	High Similarity	NPC474385
0.9343	High Similarity	NPC472601
0.9343	High Similarity	NPC472600
0.9338	High Similarity	NPC475974
0.9286	High Similarity	NPC83272
0.9281	High Similarity	NPC471731
0.9281	High Similarity	NPC159721
0.9281	High Similarity	NPC478202
0.9281	High Similarity	NPC472006
0.9275	High Similarity	NPC472035
0.9275	High Similarity	NPC472603
0.9275	High Similarity	NPC478201
0.927	High Similarity	NPC88269
0.9265	High Similarity	NPC135837
0.9265	High Similarity	NPC474771
0.9265	High Similarity	NPC194579
0.9265	High Similarity	NPC149372
0.9265	High Similarity	NPC65837
0.9265	High Similarity	NPC474849
0.9265	High Similarity	NPC178467
0.9259	High Similarity	NPC142027
0.922	High Similarity	NPC473023
0.9214	High Similarity	NPC280404
0.9214	High Similarity	NPC42540
0.9214	High Similarity	NPC210425
0.9214	High Similarity	NPC277426
0.9214	High Similarity	NPC86373
0.9214	High Similarity	NPC151607
0.9209	High Similarity	NPC471733
0.9209	High Similarity	NPC469579
0.9203	High Similarity	NPC155205
0.9191	High Similarity	NPC158481
0.9185	High Similarity	NPC175943
0.9149	High Similarity	NPC257558
0.9143	High Similarity	NPC472610
0.9137	High Similarity	NPC475730
0.9137	High Similarity	NPC37530
0.913	High Similarity	NPC275356
0.913	High Similarity	NPC52358
0.913	High Similarity	NPC247409
0.9118	High Similarity	NPC180905
0.9118	High Similarity	NPC182496
0.9118	High Similarity	NPC27407
0.9091	High Similarity	NPC221352
0.9085	High Similarity	NPC107625
0.9078	High Similarity	NPC478203
0.9078	High Similarity	NPC210966
0.9078	High Similarity	NPC126882
0.9071	High Similarity	NPC82913
0.9065	High Similarity	NPC99441
0.9058	High Similarity	NPC472403
0.9058	High Similarity	NPC9121
0.9058	High Similarity	NPC177307
0.9051	High Similarity	NPC50455
0.9051	High Similarity	NPC291454
0.9037	High Similarity	NPC476389
0.9028	High Similarity	NPC270160
0.9028	High Similarity	NPC237440
0.9021	High Similarity	NPC166583
0.9021	High Similarity	NPC472036
0.9021	High Similarity	NPC53362
0.9021	High Similarity	NPC471734
0.9021	High Similarity	NPC210320
0.9014	High Similarity	NPC472034
0.9	High Similarity	NPC90411
0.8993	High Similarity	NPC92655
0.8986	High Similarity	NPC261292
0.8986	High Similarity	NPC301915
0.8966	High Similarity	NPC56204
0.8966	High Similarity	NPC469619
0.8966	High Similarity	NPC469670
0.8963	High Similarity	NPC214702
0.8963	High Similarity	NPC470831
0.8958	High Similarity	NPC240622
0.8958	High Similarity	NPC215711
0.8958	High Similarity	NPC471642
0.8958	High Similarity	NPC471641
0.8958	High Similarity	NPC240253
0.8958	High Similarity	NPC73411
0.8951	High Similarity	NPC472033
0.8951	High Similarity	NPC471735
0.8939	High Similarity	NPC201728
0.8939	High Similarity	NPC262671
0.8936	High Similarity	NPC250755
0.8929	High Similarity	NPC165172
0.8921	High Similarity	NPC221104
0.8905	High Similarity	NPC474394
0.8904	High Similarity	NPC215921
0.8904	High Similarity	NPC200773
0.8904	High Similarity	NPC70016
0.8904	High Similarity	NPC240768
0.8897	High Similarity	NPC77325
0.8897	High Similarity	NPC476684
0.8897	High Similarity	NPC4423
0.8889	High Similarity	NPC247477
0.8889	High Similarity	NPC17840
0.8889	High Similarity	NPC14098
0.8881	High Similarity	NPC134621
0.8873	High Similarity	NPC354984
0.8865	High Similarity	NPC470842
0.8857	High Similarity	NPC471819
0.8844	High Similarity	NPC167903
0.8836	High Similarity	NPC179178
0.8828	High Similarity	NPC153417
0.8819	High Similarity	NPC237208
0.8811	High Similarity	NPC66404
0.8811	High Similarity	NPC95123
0.8794	High Similarity	NPC64664
0.8786	High Similarity	NPC126739
0.8786	High Similarity	NPC197666
0.8784	High Similarity	NPC281477
0.8784	High Similarity	NPC470102
0.8777	High Similarity	NPC156967
0.8777	High Similarity	NPC472599
0.8768	High Similarity	NPC474097
0.8759	High Similarity	NPC476463
0.8759	High Similarity	NPC8817
0.875	High Similarity	NPC29577
0.875	High Similarity	NPC296158
0.875	High Similarity	NPC312789
0.875	High Similarity	NPC473692
0.8741	High Similarity	NPC41263
0.8732	High Similarity	NPC220106
0.8732	High Similarity	NPC130485
0.8731	High Similarity	NPC95309
0.8725	High Similarity	NPC99381
0.8725	High Similarity	NPC82592
0.8725	High Similarity	NPC16082
0.8716	High Similarity	NPC478224
0.8716	High Similarity	NPC273483
0.8714	High Similarity	NPC245058
0.8707	High Similarity	NPC472891
0.8707	High Similarity	NPC475460
0.8705	High Similarity	NPC278375
0.8696	High Similarity	NPC43627
0.8696	High Similarity	NPC180261
0.8696	High Similarity	NPC37299
0.869	High Similarity	NPC470357
0.869	High Similarity	NPC267509
0.869	High Similarity	NPC225173
0.869	High Similarity	NPC163846
0.8671	High Similarity	NPC96692
0.8671	High Similarity	NPC322112
0.8671	High Similarity	NPC105648
0.8662	High Similarity	NPC168471
0.8657	High Similarity	NPC477454
0.8649	High Similarity	NPC91809
0.8643	High Similarity	NPC84699
0.8639	High Similarity	NPC233267
0.8639	High Similarity	NPC291049
0.8639	High Similarity	NPC84142
0.863	High Similarity	NPC125801
0.863	High Similarity	NPC81835
0.8621	High Similarity	NPC75694
0.8621	High Similarity	NPC32470
0.8613	High Similarity	NPC147757
0.8611	High Similarity	NPC471643
0.8611	High Similarity	NPC471639
0.8609	High Similarity	NPC190020
0.8609	High Similarity	NPC84935
0.8609	High Similarity	NPC77679
0.8603	High Similarity	NPC293453
0.8601	High Similarity	NPC149533
0.86	High Similarity	NPC478230
0.86	High Similarity	NPC170189
0.86	High Similarity	NPC208173
0.86	High Similarity	NPC69043
0.86	High Similarity	NPC199926
0.86	High Similarity	NPC79998
0.8593	High Similarity	NPC473691
0.8591	High Similarity	NPC115249
0.8591	High Similarity	NPC76041

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 NPC105456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	901
0.2-0.3	1783
0.3-0.4	2586
0.4-0.5	1948
0.5-0.6	1111
0.6-0.7	417
0.7-0.8	133
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8993	High Similarity	NPD970	Clinical (unspecified phase)
0.8621	High Similarity	NPD2532	Approved
0.8621	High Similarity	NPD2534	Approved
0.8621	High Similarity	NPD2533	Approved
0.8298	Intermediate Similarity	NPD230	Phase 1
0.8289	Intermediate Similarity	NPD7819	Suspended
0.8138	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1510	Phase 2
0.8099	Intermediate Similarity	NPD1240	Approved
0.8082	Intermediate Similarity	NPD1549	Phase 2
0.806	Intermediate Similarity	NPD9545	Approved
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1607	Approved
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6232	Discontinued
0.791	Intermediate Similarity	NPD9493	Approved
0.7898	Intermediate Similarity	NPD7075	Discontinued
0.7881	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1934	Approved
0.7862	Intermediate Similarity	NPD6959	Discontinued
0.7857	Intermediate Similarity	NPD4380	Phase 2
0.7852	Intermediate Similarity	NPD3750	Approved
0.7852	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2796	Approved
0.7823	Intermediate Similarity	NPD2935	Discontinued
0.7823	Intermediate Similarity	NPD1551	Phase 2
0.7821	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6799	Approved
0.7812	Intermediate Similarity	NPD5710	Approved
0.7812	Intermediate Similarity	NPD5711	Approved
0.7806	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6801	Discontinued
0.7755	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6599	Discontinued
0.7724	Intermediate Similarity	NPD943	Approved
0.7722	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7768	Phase 2
0.7708	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1511	Approved
0.7697	Intermediate Similarity	NPD7390	Discontinued
0.7683	Intermediate Similarity	NPD5844	Phase 1
0.7673	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3749	Approved
0.7658	Intermediate Similarity	NPD3817	Phase 2
0.7616	Intermediate Similarity	NPD4628	Phase 3
0.761	Intermediate Similarity	NPD3882	Suspended
0.7607	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6166	Phase 2
0.7597	Intermediate Similarity	NPD1512	Approved
0.7595	Intermediate Similarity	NPD2801	Approved
0.7586	Intermediate Similarity	NPD3764	Approved
0.7584	Intermediate Similarity	NPD5404	Approved
0.7584	Intermediate Similarity	NPD5406	Approved
0.7584	Intermediate Similarity	NPD5405	Approved
0.7584	Intermediate Similarity	NPD5408	Approved
0.755	Intermediate Similarity	NPD1243	Approved
0.755	Intermediate Similarity	NPD2800	Approved
0.7532	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7074	Phase 3
0.7518	Intermediate Similarity	NPD9717	Approved
0.7518	Intermediate Similarity	NPD9269	Phase 2
0.7517	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.7484	Intermediate Similarity	NPD1465	Phase 2
0.7482	Intermediate Similarity	NPD9268	Approved
0.747	Intermediate Similarity	NPD7054	Approved
0.7447	Intermediate Similarity	NPD1201	Approved
0.7438	Intermediate Similarity	NPD5402	Approved
0.7436	Intermediate Similarity	NPD5403	Approved
0.7436	Intermediate Similarity	NPD920	Approved
0.7434	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7472	Approved
0.7403	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1470	Approved
0.7361	Intermediate Similarity	NPD1164	Approved
0.7361	Intermediate Similarity	NPD1203	Approved
0.7351	Intermediate Similarity	NPD6100	Approved
0.7351	Intermediate Similarity	NPD6099	Approved
0.7347	Intermediate Similarity	NPD411	Approved
0.7342	Intermediate Similarity	NPD3226	Approved
0.7337	Intermediate Similarity	NPD7251	Discontinued
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.7324	Intermediate Similarity	NPD422	Phase 1
0.7315	Intermediate Similarity	NPD447	Suspended
0.7313	Intermediate Similarity	NPD74	Approved
0.7313	Intermediate Similarity	NPD9266	Approved
0.7312	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5401	Approved
0.7301	Intermediate Similarity	NPD919	Approved
0.7294	Intermediate Similarity	NPD7808	Phase 3
0.7285	Intermediate Similarity	NPD2799	Discontinued
0.7285	Intermediate Similarity	NPD7033	Discontinued
0.7284	Intermediate Similarity	NPD4965	Approved
0.7284	Intermediate Similarity	NPD4967	Phase 2
0.7284	Intermediate Similarity	NPD4966	Approved
0.7278	Intermediate Similarity	NPD5953	Discontinued
0.7278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1608	Approved
0.7266	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5494	Approved
0.7239	Intermediate Similarity	NPD9263	Approved
0.7239	Intermediate Similarity	NPD9264	Approved
0.7239	Intermediate Similarity	NPD9267	Approved
0.7239	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6190	Approved
0.7225	Intermediate Similarity	NPD8150	Discontinued
0.7212	Intermediate Similarity	NPD7199	Phase 2
0.7211	Intermediate Similarity	NPD6832	Phase 2
0.7208	Intermediate Similarity	NPD2654	Approved
0.7195	Intermediate Similarity	NPD6234	Discontinued
0.719	Intermediate Similarity	NPD2346	Discontinued
0.7183	Intermediate Similarity	NPD4626	Approved
0.716	Intermediate Similarity	NPD7286	Phase 2
0.7113	Intermediate Similarity	NPD5691	Approved
0.7107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD2344	Approved
0.7075	Intermediate Similarity	NPD1019	Discontinued
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7063	Intermediate Similarity	NPD1778	Approved
0.7063	Intermediate Similarity	NPD17	Approved
0.7055	Intermediate Similarity	NPD1283	Approved
0.7044	Intermediate Similarity	NPD6273	Approved
0.7025	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4288	Approved
0.7007	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD1296	Phase 2
0.7	Intermediate Similarity	NPD7228	Approved
0.7	Intermediate Similarity	NPD9281	Approved
0.7	Intermediate Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6981	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4908	Phase 1
0.6968	Remote Similarity	NPD6002	Phase 3
0.6968	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6004	Phase 3
0.6968	Remote Similarity	NPD6005	Phase 3
0.6966	Remote Similarity	NPD1610	Phase 2
0.6959	Remote Similarity	NPD2798	Approved
0.6959	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8312	Approved
0.6954	Remote Similarity	NPD520	Approved
0.6954	Remote Similarity	NPD6663	Approved
0.6954	Remote Similarity	NPD8313	Approved
0.6952	Remote Similarity	NPD8151	Discontinued
0.6949	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7003	Approved
0.694	Remote Similarity	NPD9261	Approved
0.6933	Remote Similarity	NPD3027	Phase 3
0.6923	Remote Similarity	NPD3926	Phase 2
0.6913	Remote Similarity	NPD9494	Approved
0.6913	Remote Similarity	NPD5736	Approved
0.6909	Remote Similarity	NPD5353	Approved
0.6908	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4060	Phase 1
0.6908	Remote Similarity	NPD1613	Approved
0.6905	Remote Similarity	NPD1247	Approved
0.6901	Remote Similarity	NPD3751	Discontinued
0.6899	Remote Similarity	NPD2309	Approved
0.6889	Remote Similarity	NPD6535	Approved
0.6889	Remote Similarity	NPD6534	Approved
0.6887	Remote Similarity	NPD2313	Discontinued
0.6887	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4750	Phase 3
0.6879	Remote Similarity	NPD1652	Phase 2
0.6871	Remote Similarity	NPD4749	Approved
0.6865	Remote Similarity	NPD7435	Discontinued
0.6864	Remote Similarity	NPD3787	Discontinued
0.6863	Remote Similarity	NPD6355	Discontinued
0.6852	Remote Similarity	NPD1653	Approved
0.6849	Remote Similarity	NPD1281	Approved
0.6849	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4308	Phase 3
0.6839	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8166	Discontinued
0.6829	Remote Similarity	NPD7615	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