NPASS Compound

Structure

NPC187774 OpenBabel07101719522D 40 43 0 0 1 0 0 0 0 0999 V2000 7.9778 -0.3043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3399 3.1409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5832 6.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4289 3.8839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5820 0.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7631 2.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1674 4.1418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0084 2.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7195 0.1151 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1753 1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9595 3.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 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 6.5765 0.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7576 2.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4242 4.8109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2653 3.5238 0.0000 C 0 0 0 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 7.1643 1.5228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4732 4.5019 0.0000 C 0 0 0 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 4.1808 1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6706 -0.1939 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 8.1588 1.4183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2700 5.1710 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 6.9833 -0.1997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3454 3.2454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6321 5.7891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6858 3.2147 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 35 1 0 0 0 0 3 36 1 0 0 0 0 4 37 1 0 0 0 0 5 12 2 0 0 0 0 5 17 1 0 0 0 0 6 12 1 0 0 0 0 6 18 2 0 0 0 0 7 13 2 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 20 2 0 0 0 0 9 28 1 0 0 0 0 10 38 1 0 0 0 0 11 16 1 0 0 0 0 11 39 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 10 1 6 0 0 0 15 26 1 0 0 0 0 16 21 1 0 0 0 0 16 29 1 1 0 0 0 17 22 2 0 0 0 0 17 34 1 0 0 0 0 18 22 1 0 0 0 0 18 35 1 0 0 0 0 19 23 2 0 0 0 0 19 36 1 0 0 0 0 20 23 1 0 0 0 0 20 37 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 6 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 1 0 0 0 25 12 1 6 0 0 0 25 40 1 0 0 0 0 26 13 1 1 0 0 0 26 40 1 0 0 0 0 27 38 1 6 0 0 0 27 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.22
Volume:	539.776
LogP:	0.368
LogD:	0.928
LogS:	-2.969
# Rotatable Bonds:	10
TPSA:	185.99
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	4.589
Fsp3:	0.556
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.404
MDCK Permeability:	2.0452647731872275e-05
Pgp-inhibitor:	0.093
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.564
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.212

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	50.57474899291992%
Volume Distribution (VD):	0.34
Pgp-substrate:	34.0613899230957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	3.739
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.457
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.151
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.942
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.38

Download Data

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

Natural Product: NPC187774

Natural Product ID:	NPC187774
*Common Name:**	Icariol A2 9-O-Beta-D-Xylopyranoside Icariol A2
IUPAC Name:	(2R,3R,4S,5R)-2-[[(2S,3R,4R,5S)-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	FOTVKQTYZXWNAO-KXKLIONSSA-N
Standard InCHI:	InChI=1S/C27H36O13/c1-34-17-5-12(6-18(35-2)22(17)31)25-14(9-28)15(10-38-27-24(33)21(30)16(29)11-39-27)26(40-25)13-7-19(36-3)23(32)20(8-13)37-4/h5-8,14-16,21,24-33H,9-11H2,1-4H3/t14-,15-,16+,21-,24+,25+,26+,27+/m0/s1
SMILES:	COc1cc(cc(c1O)OC)[C@@H]1[C@@H](CO)[C@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)[C@@H](c2cc(c(c(c2)OC)O)OC)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511898
PubChem CID:	44577146
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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
NPO33006	neoalsomitra integrifoliola	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18396904]

☑ 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.	Inhibition	=	4.67	%	PMID[448910]

☑ 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 NPC187774 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	409
0.1-0.2	1410
0.2-0.3	3646
0.3-0.4	9270
0.4-0.5	9534
0.5-0.6	5544
0.6-0.7	7863
0.7-0.8	3737
0.8-0.85	831
0.85-0.9	348
0.9-0.95	96
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472712
1.0	High Similarity	NPC472713
1.0	High Similarity	NPC118385
1.0	High Similarity	NPC473046
0.9853	High Similarity	NPC5262
0.9853	High Similarity	NPC472714
0.9784	High Similarity	NPC39657
0.9714	High Similarity	NPC248132
0.9714	High Similarity	NPC130449
0.9645	High Similarity	NPC55158
0.9645	High Similarity	NPC51328
0.9645	High Similarity	NPC286235
0.9635	High Similarity	NPC472711
0.9577	High Similarity	NPC472709
0.9577	High Similarity	NPC472710
0.9559	High Similarity	NPC474039
0.9496	High Similarity	NPC185307
0.9496	High Similarity	NPC477898
0.9496	High Similarity	NPC470950
0.9429	High Similarity	NPC25292
0.9429	High Similarity	NPC84181
0.9429	High Similarity	NPC129417
0.9429	High Similarity	NPC283995
0.9429	High Similarity	NPC470235
0.9429	High Similarity	NPC473045
0.9424	High Similarity	NPC469559
0.9424	High Similarity	NPC476356
0.9424	High Similarity	NPC189115
0.942	High Similarity	NPC177868
0.9412	High Similarity	NPC236522
0.9362	High Similarity	NPC279298
0.9362	High Similarity	NPC38041
0.9362	High Similarity	NPC475096
0.9362	High Similarity	NPC22150
0.9357	High Similarity	NPC473044
0.9357	High Similarity	NPC185071
0.9357	High Similarity	NPC12728
0.9357	High Similarity	NPC46092
0.9353	High Similarity	NPC469661
0.9343	High Similarity	NPC199459
0.9343	High Similarity	NPC52277
0.9343	High Similarity	NPC177035
0.9338	High Similarity	NPC244983
0.9338	High Similarity	NPC107478
0.9338	High Similarity	NPC326095
0.9306	High Similarity	NPC218041
0.9306	High Similarity	NPC225815
0.9306	High Similarity	NPC260781
0.9306	High Similarity	NPC469707
0.9306	High Similarity	NPC185955
0.9306	High Similarity	NPC9933
0.9306	High Similarity	NPC214326
0.9306	High Similarity	NPC145979
0.9306	High Similarity	NPC469706
0.9306	High Similarity	NPC182368
0.9301	High Similarity	NPC270751
0.9296	High Similarity	NPC112861
0.9296	High Similarity	NPC99515
0.9296	High Similarity	NPC190714
0.9296	High Similarity	NPC212890
0.9275	High Similarity	NPC195196
0.9275	High Similarity	NPC283949
0.927	High Similarity	NPC184938
0.927	High Similarity	NPC101624
0.9236	High Similarity	NPC35877
0.9236	High Similarity	NPC55715
0.9236	High Similarity	NPC95392
0.9231	High Similarity	NPC275284
0.9231	High Similarity	NPC15956
0.9231	High Similarity	NPC193473
0.9231	High Similarity	NPC31325
0.9231	High Similarity	NPC114505
0.9231	High Similarity	NPC213074
0.9231	High Similarity	NPC227902
0.9231	High Similarity	NPC224674
0.9225	High Similarity	NPC18979
0.9225	High Similarity	NPC307466
0.9225	High Similarity	NPC161700
0.9225	High Similarity	NPC477702
0.9225	High Similarity	NPC277867
0.922	High Similarity	NPC255566
0.922	High Similarity	NPC298317
0.922	High Similarity	NPC278961
0.922	High Similarity	NPC113680
0.9209	High Similarity	NPC212770
0.9209	High Similarity	NPC98777
0.9209	High Similarity	NPC156376
0.9197	High Similarity	NPC287745
0.9191	High Similarity	NPC175067
0.9191	High Similarity	NPC204215
0.9191	High Similarity	NPC470270
0.9167	High Similarity	NPC175976
0.9161	High Similarity	NPC125755
0.9149	High Similarity	NPC246947
0.9149	High Similarity	NPC475084
0.9143	High Similarity	NPC226547
0.9143	High Similarity	NPC56091
0.9143	High Similarity	NPC46591
0.9137	High Similarity	NPC65530
0.9137	High Similarity	NPC304152
0.9137	High Similarity	NPC138738
0.9137	High Similarity	NPC470413
0.9137	High Similarity	NPC185908
0.9137	High Similarity	NPC59324
0.913	High Similarity	NPC24490
0.913	High Similarity	NPC150534
0.913	High Similarity	NPC141765
0.913	High Similarity	NPC34103
0.913	High Similarity	NPC165155
0.9124	High Similarity	NPC158331
0.9124	High Similarity	NPC196937
0.9124	High Similarity	NPC132895
0.9091	High Similarity	NPC43508
0.9091	High Similarity	NPC166506
0.9091	High Similarity	NPC286245
0.9091	High Similarity	NPC110763
0.9091	High Similarity	NPC272619
0.9091	High Similarity	NPC197352
0.9091	High Similarity	NPC189239
0.9091	High Similarity	NPC476301
0.9085	High Similarity	NPC37793
0.9085	High Similarity	NPC81638
0.9078	High Similarity	NPC471908
0.9071	High Similarity	NPC30951
0.9071	High Similarity	NPC6369
0.9065	High Similarity	NPC172818
0.9065	High Similarity	NPC25695
0.9065	High Similarity	NPC203230
0.9065	High Similarity	NPC242028
0.9058	High Similarity	NPC48863
0.9058	High Similarity	NPC470881
0.9058	High Similarity	NPC13745
0.9058	High Similarity	NPC251981
0.9058	High Similarity	NPC35731
0.9051	High Similarity	NPC106739
0.9051	High Similarity	NPC253105
0.9051	High Similarity	NPC201587
0.9051	High Similarity	NPC471505
0.9048	High Similarity	NPC302610
0.9041	High Similarity	NPC98624
0.9041	High Similarity	NPC475224
0.9034	High Similarity	NPC301961
0.9034	High Similarity	NPC166584
0.9028	High Similarity	NPC226540
0.9021	High Similarity	NPC471415
0.9021	High Similarity	NPC469313
0.9021	High Similarity	NPC76176
0.9021	High Similarity	NPC121661
0.9021	High Similarity	NPC471667
0.9021	High Similarity	NPC470097
0.9021	High Similarity	NPC217635
0.9021	High Similarity	NPC114119
0.9021	High Similarity	NPC253015
0.9021	High Similarity	NPC471065
0.9021	High Similarity	NPC168579
0.9021	High Similarity	NPC79429
0.9021	High Similarity	NPC471063
0.9021	High Similarity	NPC138227
0.9021	High Similarity	NPC73467
0.9014	High Similarity	NPC41782
0.9014	High Similarity	NPC48309
0.9014	High Similarity	NPC287124
0.9007	High Similarity	NPC309124
0.9007	High Similarity	NPC291101
0.9007	High Similarity	NPC266197
0.9007	High Similarity	NPC106944
0.9007	High Similarity	NPC184797
0.9007	High Similarity	NPC284464
0.8993	High Similarity	NPC142547
0.8993	High Similarity	NPC126409
0.8993	High Similarity	NPC135777
0.8993	High Similarity	NPC99572
0.8986	High Similarity	NPC215833
0.8986	High Similarity	NPC6836
0.8986	High Similarity	NPC69513
0.8978	High Similarity	NPC476345
0.8978	High Similarity	NPC65942
0.8978	High Similarity	NPC470096
0.8978	High Similarity	NPC474017
0.8978	High Similarity	NPC475067
0.8978	High Similarity	NPC248307
0.8978	High Similarity	NPC470095
0.8973	High Similarity	NPC90896
0.8973	High Similarity	NPC283839
0.8973	High Similarity	NPC106138
0.8966	High Similarity	NPC473480
0.8966	High Similarity	NPC15538
0.8958	High Similarity	NPC469586
0.8951	High Similarity	NPC324962
0.8951	High Similarity	NPC252169
0.8951	High Similarity	NPC474808
0.8944	High Similarity	NPC247291
0.8944	High Similarity	NPC311530
0.8936	High Similarity	NPC236306
0.8936	High Similarity	NPC193666
0.8936	High Similarity	NPC292487
0.8936	High Similarity	NPC123526
0.8936	High Similarity	NPC473739
0.8936	High Similarity	NPC88640
0.8936	High Similarity	NPC232164

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 NPC187774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	773
0.2-0.3	1832
0.3-0.4	2924
0.4-0.5	1727
0.5-0.6	1051
0.6-0.7	442
0.7-0.8	72
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8832	High Similarity	NPD3027	Phase 3
0.8662	High Similarity	NPD7228	Approved
0.8571	High Similarity	NPD6234	Discontinued
0.8511	High Similarity	NPD1612	Clinical (unspecified phase)
0.8511	High Similarity	NPD1613	Approved
0.8487	Intermediate Similarity	NPD37	Approved
0.8442	Intermediate Similarity	NPD4967	Phase 2
0.8442	Intermediate Similarity	NPD4965	Approved
0.8442	Intermediate Similarity	NPD4966	Approved
0.8288	Intermediate Similarity	NPD7266	Discontinued
0.8286	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD6674	Discontinued
0.8116	Intermediate Similarity	NPD3705	Approved
0.811	Intermediate Similarity	NPD7240	Approved
0.8098	Intermediate Similarity	NPD7074	Phase 3
0.8086	Intermediate Similarity	NPD3818	Discontinued
0.8037	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7988	Intermediate Similarity	NPD7472	Approved
0.7847	Intermediate Similarity	NPD4908	Phase 1
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.777	Intermediate Similarity	NPD1357	Approved
0.7755	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3620	Phase 2
0.774	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7808	Phase 3
0.773	Intermediate Similarity	NPD1610	Phase 2
0.773	Intermediate Similarity	NPD1091	Approved
0.7727	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6797	Phase 2
0.7679	Intermediate Similarity	NPD7685	Pre-registration
0.7673	Intermediate Similarity	NPD1934	Approved
0.7655	Intermediate Similarity	NPD2861	Phase 2
0.7647	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2983	Phase 2
0.7622	Intermediate Similarity	NPD2982	Phase 2
0.7619	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6559	Discontinued
0.7556	Intermediate Similarity	NPD7680	Approved
0.7552	Intermediate Similarity	NPD2981	Phase 2
0.7548	Intermediate Similarity	NPD5058	Phase 3
0.7534	Intermediate Similarity	NPD3018	Phase 2
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2978	Approved
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2977	Approved
0.75	Intermediate Similarity	NPD4749	Approved
0.7469	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD228	Approved
0.7396	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5125	Phase 3
0.7343	Intermediate Similarity	NPD5126	Approved
0.7324	Intermediate Similarity	NPD1548	Phase 1
0.7317	Intermediate Similarity	NPD3882	Suspended
0.7315	Intermediate Similarity	NPD4625	Phase 3
0.7301	Intermediate Similarity	NPD2801	Approved
0.7301	Intermediate Similarity	NPD8455	Phase 2
0.7299	Intermediate Similarity	NPD3021	Approved
0.7299	Intermediate Similarity	NPD3022	Approved
0.7267	Intermediate Similarity	NPD4005	Discontinued
0.7261	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7157	Approved
0.7222	Intermediate Similarity	NPD4380	Phase 2
0.7216	Intermediate Similarity	NPD6841	Approved
0.7216	Intermediate Similarity	NPD6842	Approved
0.7216	Intermediate Similarity	NPD6843	Phase 3
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4108	Discontinued
0.7208	Intermediate Similarity	NPD5588	Approved
0.7195	Intermediate Similarity	NPD1465	Phase 2
0.7193	Intermediate Similarity	NPD5844	Phase 1
0.7186	Intermediate Similarity	NPD5494	Approved
0.7176	Intermediate Similarity	NPD7473	Discontinued
0.7171	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD4536	Approved
0.7143	Intermediate Similarity	NPD4538	Approved
0.7143	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7843	Approved
0.7134	Intermediate Similarity	NPD4236	Phase 3
0.7134	Intermediate Similarity	NPD4237	Approved
0.7134	Intermediate Similarity	NPD3384	Approved
0.7134	Intermediate Similarity	NPD3382	Approved
0.7134	Intermediate Similarity	NPD5177	Phase 3
0.7134	Intermediate Similarity	NPD3383	Approved
0.7124	Intermediate Similarity	NPD5735	Approved
0.7115	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1375	Discontinued
0.7107	Intermediate Similarity	NPD7124	Phase 2
0.7101	Intermediate Similarity	NPD6232	Discontinued
0.7066	Intermediate Similarity	NPD7075	Discontinued
0.7063	Intermediate Similarity	NPD1511	Approved
0.7059	Intermediate Similarity	NPD1558	Phase 1
0.7051	Intermediate Similarity	NPD6099	Approved
0.7051	Intermediate Similarity	NPD6100	Approved
0.7039	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7032	Intermediate Similarity	NPD6111	Discontinued
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7025	Intermediate Similarity	NPD3060	Approved
0.7013	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD230	Phase 1
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD5124	Phase 1
0.7012	Intermediate Similarity	NPD4675	Approved
0.7012	Intermediate Similarity	NPD4678	Approved
0.7006	Intermediate Similarity	NPD3540	Phase 1
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3787	Discontinued
0.6987	Remote Similarity	NPD5960	Phase 3
0.6981	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6331	Phase 2
0.6981	Remote Similarity	NPD4110	Phase 3
0.698	Remote Similarity	NPD8651	Approved
0.6978	Remote Similarity	NPD2684	Approved
0.6975	Remote Similarity	NPD1512	Approved
0.6974	Remote Similarity	NPD7095	Approved
0.6968	Remote Similarity	NPD6653	Approved
0.6957	Remote Similarity	NPD4357	Discontinued
0.6948	Remote Similarity	NPD2238	Phase 2
0.6946	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3539	Phase 1
0.6941	Remote Similarity	NPD8127	Discontinued
0.6933	Remote Similarity	NPD3094	Phase 2
0.6932	Remote Similarity	NPD7549	Discontinued
0.6928	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7906	Approved
0.6923	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD27	Approved
0.6919	Remote Similarity	NPD2489	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7447	Phase 1
0.6913	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7028	Phase 2
0.6906	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3657	Discovery
0.6893	Remote Similarity	NPD7313	Approved
0.6893	Remote Similarity	NPD7312	Approved
0.6893	Remote Similarity	NPD8312	Approved
0.6893	Remote Similarity	NPD7311	Approved
0.6893	Remote Similarity	NPD7310	Approved
0.6893	Remote Similarity	NPD8313	Approved
0.6889	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7819	Suspended
0.6886	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5773	Approved
0.6886	Remote Similarity	NPD5772	Approved
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3892	Phase 2
0.6875	Remote Similarity	NPD7466	Approved
0.6875	Remote Similarity	NPD4628	Phase 3
0.6875	Remote Similarity	NPD6671	Approved
0.6872	Remote Similarity	NPD4663	Approved
0.6867	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5604	Discontinued
0.686	Remote Similarity	NPD2970	Approved
0.686	Remote Similarity	NPD2969	Approved
0.6854	Remote Similarity	NPD8054	Approved
0.6854	Remote Similarity	NPD7309	Approved
0.6854	Remote Similarity	NPD8053	Approved
0.6852	Remote Similarity	NPD7212	Phase 2
0.6852	Remote Similarity	NPD7213	Phase 3
0.6839	Remote Similarity	NPD3751	Discontinued
0.6839	Remote Similarity	NPD4140	Approved
0.6833	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2219	Phase 1
0.681	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4750	Phase 3
0.6802	Remote Similarity	NPD3051	Approved
0.6802	Remote Similarity	NPD6071	Discontinued
0.6802	Remote Similarity	NPD7229	Phase 3
0.68	Remote Similarity	NPD5327	Phase 3
0.6798	Remote Similarity	NPD4578	Approved
0.6798	Remote Similarity	NPD4577	Approved
0.6792	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7827	Phase 1

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