NPASS Compound

Structure

NPC188555 OpenBabel07101718312D 37 40 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 5 1 0 0 0 0 3 12 2 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 26 1 0 0 0 0 11 17 1 0 0 0 0 11 34 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 35 1 0 0 0 0 17 19 1 0 0 0 0 17 29 1 6 0 0 0 18 10 1 1 0 0 0 18 20 1 0 0 0 0 18 36 1 0 0 0 0 19 23 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 31 1 6 0 0 0 21 22 1 0 0 0 0 21 32 1 1 0 0 0 22 24 1 0 0 0 0 22 33 1 6 0 0 0 23 25 1 0 0 0 0 23 37 1 6 0 0 0 24 36 1 0 0 0 0 24 37 1 1 0 0 0 25 34 1 0 0 0 0 25 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.17
Volume:	493.758
LogP:	0.416
LogD:	0.284
LogS:	-2.202
# Rotatable Bonds:	7
TPSA:	198.76
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	4.464
Fsp3:	0.44
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.412
MDCK Permeability:	1.027613598125754e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.905
20% Bioavailability (F20%):	0.232
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	96.1501235961914%
Volume Distribution (VD):	0.398
Pgp-substrate:	3.2085940837860107%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	1.267
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.464
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.177
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.955
Carcinogencity:	0.112
Eye Corrosion:	0.003
Eye Irritation:	0.083
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC188555

Natural Product ID:	NPC188555
*Common Name:**	Lysidiside M
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R)-4,5-dihydroxy-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	lysidiside M
Standard InCHIKey:	KTSPZJPSJGQOIQ-YKULTYPDSA-N
Standard InCHI:	InChI=1S/C25H30O12/c26-10-18-20(31)21(32)22(33)24(36-18)37-23-19(30)17(29)11-34-25(23)35-16-8-13(7-15(28)9-16)2-1-12-3-5-14(27)6-4-12/h1-9,17-33H,10-11H2/b2-1+/t17-,18-,19+,20-,21+,22-,23-,24+,25+/m1/s1
SMILES:	C(=Cc1cc(cc(c1)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573408
PubChem CID:	25155595
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene glycosides

*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
NPO33047	lysidice brevicalyx wei	Species	n.a.	Eukaryota	Barks	n.a.	n.a.	PMID[18847246]

☑ 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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	5.0	%	PMID[506406]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	29.0	%	PMID[506406]

☑ 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 NPC188555 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	449
0.1-0.2	1740
0.2-0.3	5029
0.3-0.4	11043
0.4-0.5	7040
0.5-0.6	5579
0.6-0.7	7655
0.7-0.8	3566
0.8-0.85	448
0.85-0.9	109
0.9-0.95	25
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC130496
0.9922	High Similarity	NPC238243
0.9845	High Similarity	NPC40664
0.9845	High Similarity	NPC197723
0.9845	High Similarity	NPC165482
0.9845	High Similarity	NPC138350
0.9845	High Similarity	NPC3293
0.9843	High Similarity	NPC303422
0.9843	High Similarity	NPC26080
0.9843	High Similarity	NPC85799
0.9843	High Similarity	NPC165686
0.9766	High Similarity	NPC294166
0.9766	High Similarity	NPC115022
0.9764	High Similarity	NPC121376
0.9606	High Similarity	NPC218003
0.9549	High Similarity	NPC257095
0.9549	High Similarity	NPC89686
0.9549	High Similarity	NPC273932
0.9542	High Similarity	NPC203230
0.9542	High Similarity	NPC242028
0.947	High Similarity	NPC124149
0.947	High Similarity	NPC59324
0.947	High Similarity	NPC65530
0.9398	High Similarity	NPC212770
0.9398	High Similarity	NPC98777
0.9338	High Similarity	NPC76176
0.9338	High Similarity	NPC138227
0.9338	High Similarity	NPC469313
0.9338	High Similarity	NPC168579
0.9323	High Similarity	NPC87777
0.9323	High Similarity	NPC262328
0.9265	High Similarity	NPC37793
0.9259	High Similarity	NPC210192
0.9259	High Similarity	NPC469661
0.9248	High Similarity	NPC164857
0.9203	High Similarity	NPC125755
0.9191	High Similarity	NPC189115
0.9191	High Similarity	NPC475084
0.9191	High Similarity	NPC469559
0.9191	High Similarity	NPC472353
0.9173	High Similarity	NPC470236
0.9167	High Similarity	NPC49074
0.916	High Similarity	NPC475067
0.9141	High Similarity	NPC12308
0.9137	High Similarity	NPC473480
0.9137	High Similarity	NPC15538
0.913	High Similarity	NPC161700
0.913	High Similarity	NPC277867
0.9124	High Similarity	NPC473044
0.9124	High Similarity	NPC252169
0.9091	High Similarity	NPC162093
0.9071	High Similarity	NPC280945
0.9058	High Similarity	NPC473045
0.9058	High Similarity	NPC25292
0.9051	High Similarity	NPC139976
0.9051	High Similarity	NPC49542
0.9051	High Similarity	NPC84207
0.9051	High Similarity	NPC230718
0.9051	High Similarity	NPC128337
0.9051	High Similarity	NPC5253
0.9044	High Similarity	NPC106944
0.9037	High Similarity	NPC134260
0.9023	High Similarity	NPC132895
0.8993	High Similarity	NPC475096
0.8978	High Similarity	NPC108674
0.8955	High Similarity	NPC13745
0.8955	High Similarity	NPC251981
0.8955	High Similarity	NPC48863
0.8947	High Similarity	NPC299144
0.8939	High Similarity	NPC262606
0.8929	High Similarity	NPC190714
0.8929	High Similarity	NPC99515
0.8921	High Similarity	NPC225445
0.8897	High Similarity	NPC470413
0.8897	High Similarity	NPC138738
0.8889	High Similarity	NPC185778
0.8881	High Similarity	NPC473621
0.8881	High Similarity	NPC69513
0.8881	High Similarity	NPC215833
0.8872	High Similarity	NPC473412
0.8872	High Similarity	NPC9912
0.8872	High Similarity	NPC469698
0.8865	High Similarity	NPC227902
0.8865	High Similarity	NPC39657
0.8864	High Similarity	NPC248355
0.8849	High Similarity	NPC116922
0.8824	High Similarity	NPC172818
0.8824	High Similarity	NPC25695
0.8815	High Similarity	NPC170694
0.8815	High Similarity	NPC476411
0.8815	High Similarity	NPC187194
0.8815	High Similarity	NPC87696
0.8815	High Similarity	NPC107478
0.8806	High Similarity	NPC470270
0.8803	High Similarity	NPC478237
0.8803	High Similarity	NPC175976
0.8794	High Similarity	NPC74320
0.8794	High Similarity	NPC107120
0.8788	High Similarity	NPC302378
0.8788	High Similarity	NPC40377
0.8786	High Similarity	NPC177597
0.8786	High Similarity	NPC476867
0.8777	High Similarity	NPC5262
0.8777	High Similarity	NPC145319
0.8777	High Similarity	NPC472714
0.8759	High Similarity	NPC195196
0.875	High Similarity	NPC79957
0.875	High Similarity	NPC269242
0.875	High Similarity	NPC469412
0.875	High Similarity	NPC198734
0.8741	High Similarity	NPC51328
0.8741	High Similarity	NPC286235
0.8741	High Similarity	NPC106138
0.8741	High Similarity	NPC55158
0.8723	High Similarity	NPC476869
0.8723	High Similarity	NPC476866
0.8723	High Similarity	NPC226722
0.8723	High Similarity	NPC476868
0.8723	High Similarity	NPC476864
0.8722	High Similarity	NPC166040
0.8722	High Similarity	NPC307110
0.8705	High Similarity	NPC186406
0.8696	High Similarity	NPC292487
0.869	High Similarity	NPC233467
0.869	High Similarity	NPC169404
0.869	High Similarity	NPC21902
0.869	High Similarity	NPC53587
0.869	High Similarity	NPC59692
0.869	High Similarity	NPC176186
0.8686	High Similarity	NPC177035
0.8686	High Similarity	NPC166180
0.8686	High Similarity	NPC104167
0.8686	High Similarity	NPC199459
0.8686	High Similarity	NPC52277
0.8681	High Similarity	NPC238140
0.8676	High Similarity	NPC35731
0.8672	High Similarity	NPC469708
0.8672	High Similarity	NPC60589
0.8671	High Similarity	NPC130449
0.8671	High Similarity	NPC248132
0.8667	High Similarity	NPC7903
0.8667	High Similarity	NPC16208
0.8667	High Similarity	NPC35932
0.8667	High Similarity	NPC184447
0.8667	High Similarity	NPC160991
0.8667	High Similarity	NPC254275
0.8662	High Similarity	NPC155564
0.8662	High Similarity	NPC248053
0.8662	High Similarity	NPC476865
0.8662	High Similarity	NPC102280
0.8657	High Similarity	NPC80600
0.8657	High Similarity	NPC472024
0.8652	High Similarity	NPC472713
0.8652	High Similarity	NPC187774
0.8652	High Similarity	NPC292443
0.8652	High Similarity	NPC118385
0.8652	High Similarity	NPC473046
0.8652	High Similarity	NPC472712
0.8643	High Similarity	NPC157816
0.8633	High Similarity	NPC210478
0.8633	High Similarity	NPC202700
0.863	High Similarity	NPC78809
0.863	High Similarity	NPC150442
0.8626	High Similarity	NPC287429
0.8623	High Similarity	NPC211549
0.8621	High Similarity	NPC259707
0.8615	High Similarity	NPC476142
0.8613	High Similarity	NPC61946
0.8613	High Similarity	NPC164787
0.8611	High Similarity	NPC35877
0.8611	High Similarity	NPC95392
0.8611	High Similarity	NPC55715
0.8603	High Similarity	NPC215037
0.8603	High Similarity	NPC25821
0.8601	High Similarity	NPC52740
0.8593	High Similarity	NPC469625
0.8593	High Similarity	NPC65942
0.8593	High Similarity	NPC166168
0.8593	High Similarity	NPC469613
0.8593	High Similarity	NPC248307
0.8593	High Similarity	NPC472597
0.8593	High Similarity	NPC103799
0.8593	High Similarity	NPC30043
0.8592	High Similarity	NPC23807
0.8582	High Similarity	NPC273295
0.8582	High Similarity	NPC81638
0.8582	High Similarity	NPC185307
0.8582	High Similarity	NPC97326
0.8582	High Similarity	NPC478239
0.8582	High Similarity	NPC470950
0.8582	High Similarity	NPC46092
0.8582	High Similarity	NPC190629
0.8582	High Similarity	NPC218856
0.8582	High Similarity	NPC202582
0.8582	High Similarity	NPC285339
0.8582	High Similarity	NPC226788
0.8582	High Similarity	NPC270849
0.8582	High Similarity	NPC26653
0.8582	High Similarity	NPC470258
0.8582	High Similarity	NPC210623

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 NPC188555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	846
0.2-0.3	1937
0.3-0.4	2885
0.4-0.5	1662
0.5-0.6	976
0.6-0.7	430
0.7-0.8	60
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8538	High Similarity	NPD1091	Approved
0.8529	High Similarity	NPD1613	Approved
0.8529	High Similarity	NPD1612	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1653	Approved
0.8309	Intermediate Similarity	NPD3027	Phase 3
0.8235	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD7266	Discontinued
0.8162	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD4908	Phase 1
0.8038	Intermediate Similarity	NPD7054	Approved
0.7987	Intermediate Similarity	NPD7472	Approved
0.7987	Intermediate Similarity	NPD7074	Phase 3
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD1610	Phase 2
0.7955	Intermediate Similarity	NPD1548	Phase 1
0.7937	Intermediate Similarity	NPD6797	Phase 2
0.7888	Intermediate Similarity	NPD7251	Discontinued
0.784	Intermediate Similarity	NPD7808	Phase 3
0.7812	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2861	Phase 2
0.775	Intermediate Similarity	NPD3818	Discontinued
0.775	Intermediate Similarity	NPD7228	Approved
0.773	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8455	Phase 2
0.7687	Intermediate Similarity	NPD6674	Discontinued
0.7669	Intermediate Similarity	NPD6559	Discontinued
0.7651	Intermediate Similarity	NPD5058	Phase 3
0.7628	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD2983	Phase 2
0.7609	Intermediate Similarity	NPD2982	Phase 2
0.7548	Intermediate Similarity	NPD37	Approved
0.7536	Intermediate Similarity	NPD2981	Phase 2
0.7535	Intermediate Similarity	NPD4625	Phase 3
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.7532	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4965	Approved
0.7516	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD1357	Approved
0.7483	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4749	Approved
0.7466	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4538	Approved
0.7466	Intermediate Similarity	NPD4536	Approved
0.745	Intermediate Similarity	NPD1652	Phase 2
0.745	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7199	Phase 2
0.7436	Intermediate Similarity	NPD1934	Approved
0.7415	Intermediate Similarity	NPD5960	Phase 3
0.7415	Intermediate Similarity	NPD5588	Approved
0.7394	Intermediate Similarity	NPD3018	Phase 2
0.7391	Intermediate Similarity	NPD3787	Discontinued
0.7389	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7843	Approved
0.7361	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7240	Approved
0.7342	Intermediate Similarity	NPD5402	Approved
0.7338	Intermediate Similarity	NPD3705	Approved
0.7333	Intermediate Similarity	NPD7157	Approved
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2684	Approved
0.7323	Intermediate Similarity	NPD1242	Phase 1
0.7308	Intermediate Similarity	NPD968	Approved
0.7289	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4060	Phase 1
0.7255	Intermediate Similarity	NPD7212	Phase 2
0.7255	Intermediate Similarity	NPD7213	Phase 3
0.7252	Intermediate Similarity	NPD290	Approved
0.725	Intermediate Similarity	NPD7075	Discontinued
0.7239	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7097	Phase 1
0.7226	Intermediate Similarity	NPD5403	Approved
0.7214	Intermediate Similarity	NPD422	Phase 1
0.7212	Intermediate Similarity	NPD3751	Discontinued
0.7208	Intermediate Similarity	NPD7447	Phase 1
0.72	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6516	Phase 2
0.7194	Intermediate Similarity	NPD5846	Approved
0.7192	Intermediate Similarity	NPD6233	Phase 2
0.717	Intermediate Similarity	NPD2801	Approved
0.716	Intermediate Similarity	NPD8313	Approved
0.716	Intermediate Similarity	NPD8312	Approved
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD1511	Approved
0.7125	Intermediate Similarity	NPD3817	Phase 2
0.7124	Intermediate Similarity	NPD6190	Approved
0.7113	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5401	Approved
0.7097	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4340	Discontinued
0.7089	Intermediate Similarity	NPD4678	Approved
0.7089	Intermediate Similarity	NPD4675	Approved
0.7083	Intermediate Similarity	NPD6584	Phase 3
0.708	Intermediate Similarity	NPD6671	Approved
0.7071	Intermediate Similarity	NPD5125	Phase 3
0.7071	Intermediate Similarity	NPD5126	Approved
0.7067	Intermediate Similarity	NPD4108	Discontinued
0.7066	Intermediate Similarity	NPD5844	Phase 1
0.7063	Intermediate Similarity	NPD1465	Phase 2
0.7063	Intermediate Similarity	NPD8651	Approved
0.7063	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD3750	Approved
0.7055	Intermediate Similarity	NPD7095	Approved
0.7051	Intermediate Similarity	NPD1512	Approved
0.7042	Intermediate Similarity	NPD2231	Phase 2
0.7042	Intermediate Similarity	NPD2235	Phase 2
0.7037	Intermediate Similarity	NPD228	Approved
0.7037	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6959	Discontinued
0.7007	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6801	Discontinued
0.6987	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5735	Approved
0.6975	Remote Similarity	NPD3882	Suspended
0.6966	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2977	Approved
0.6957	Remote Similarity	NPD2978	Approved
0.6957	Remote Similarity	NPD7819	Suspended
0.6948	Remote Similarity	NPD4535	Phase 3
0.6948	Remote Similarity	NPD3892	Phase 2
0.6944	Remote Similarity	NPD3225	Approved
0.6937	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7411	Suspended
0.6934	Remote Similarity	NPD5283	Phase 1
0.6933	Remote Similarity	NPD6653	Approved
0.6927	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6799	Approved
0.6914	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1558	Phase 1
0.6908	Remote Similarity	NPD1551	Phase 2
0.6908	Remote Similarity	NPD6100	Approved
0.6908	Remote Similarity	NPD6099	Approved
0.6903	Remote Similarity	NPD2677	Approved
0.6875	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6582	Phase 2
0.6875	Remote Similarity	NPD3685	Discontinued
0.6875	Remote Similarity	NPD6583	Phase 3
0.6868	Remote Similarity	NPD7680	Approved
0.6867	Remote Similarity	NPD6355	Discontinued
0.6863	Remote Similarity	NPD5763	Approved
0.6863	Remote Similarity	NPD5762	Approved
0.6863	Remote Similarity	NPD3540	Phase 1
0.6861	Remote Similarity	NPD5535	Approved
0.6852	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5494	Approved
0.6846	Remote Similarity	NPD4062	Phase 3
0.6842	Remote Similarity	NPD1510	Phase 2
0.6842	Remote Similarity	NPD7033	Discontinued
0.6839	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3179	Approved
0.6824	Remote Similarity	NPD3180	Approved
0.6818	Remote Similarity	NPD2424	Discontinued
0.6815	Remote Similarity	NPD4357	Discontinued
0.6813	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1182	Approved
0.68	Remote Similarity	NPD2238	Phase 2
0.68	Remote Similarity	NPD4140	Approved
0.68	Remote Similarity	NPD6841	Approved
0.68	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3620	Phase 2
0.68	Remote Similarity	NPD6843	Phase 3
0.68	Remote Similarity	NPD6842	Approved
0.6797	Remote Similarity	NPD3454	Phase 3
0.6797	Remote Similarity	NPD3539	Phase 1
0.6797	Remote Similarity	NPD2796	Approved
0.6795	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2122	Discontinued
0.6783	Remote Similarity	NPD3496	Discontinued
0.6782	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5061	Approved
0.6774	Remote Similarity	NPD5062	Approved
0.6774	Remote Similarity	NPD3060	Approved
0.6772	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3536	Discontinued
0.6772	Remote Similarity	NPD4123	Phase 3
0.6768	Remote Similarity	NPD7768	Phase 2
0.6761	Remote Similarity	NPD5585	Approved
0.6759	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD230	Phase 1
0.6753	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1375	Discontinued
0.6742	Remote Similarity	NPD291	Approved
0.6741	Remote Similarity	NPD1358	Approved
0.6738	Remote Similarity	NPD5536	Phase 2
0.6736	Remote Similarity	NPD1535	Discovery
0.6732	Remote Similarity	NPD3748	Approved
0.6731	Remote Similarity	NPD7466	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