NPASS Compound

Structure

CID15815 OpenBabel06191715342D 43 47 0 0 1 0 0 0 0 0999 V2000 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 1 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 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 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 42 1 0 0 0 0 2 10 1 0 0 0 0 2 21 2 0 0 0 0 3 11 2 0 0 0 0 3 21 1 0 0 0 0 4 12 1 0 0 0 0 4 22 2 0 0 0 0 5 13 2 0 0 0 0 5 22 1 0 0 0 0 6 14 1 0 0 0 0 6 21 1 0 0 0 0 7 17 2 0 0 0 0 7 22 1 0 0 0 0 8 15 1 0 0 0 0 8 23 2 0 0 0 0 9 16 2 0 0 0 0 9 23 1 0 0 0 0 10 25 2 0 0 0 0 11 25 1 0 0 0 0 12 26 2 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 27 2 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 28 1 0 0 0 0 19 24 1 0 0 0 0 19 31 1 0 0 0 0 20 30 2 0 0 0 0 20 32 1 0 0 0 0 24 18 1 1 0 0 0 24 33 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 38 1 0 0 0 0 28 39 1 6 0 0 0 29 34 1 0 0 0 0 29 40 2 0 0 0 0 30 33 1 0 0 0 0 30 41 1 0 0 0 0 31 23 1 1 0 0 0 31 43 1 0 0 0 0 32 34 2 0 0 0 0 32 42 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 35 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.23
Volume:	604.545
LogP:	5.114
LogD:	3.872
LogS:	-4.325
# Rotatable Bonds:	10
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.107
Synthetic Accessibility Score:	3.985
Fsp3:	0.229
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:	-5.137
MDCK Permeability:	6.75757792123477e-06
Pgp-inhibitor:	0.033
Pgp-substrate:	0.809
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	101.06343841552734%
Volume Distribution (VD):	0.227
Pgp-substrate:	0.6532388925552368%

ADMET: Metabolism

CYP1A2-inhibitor:	0.432
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.944
CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.61
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	10.874
Half-life (T1/2):	0.722

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.412
Drug-inuced Liver Injury (DILI):	0.751
AMES Toxicity:	0.492
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.959
Carcinogencity:	0.445
Eye Corrosion:	0.003
Eye Irritation:	0.878
Respiratory Toxicity:	0.542

Download Data

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

Natural Product: NPC15815

Natural Product ID:	NPC15815
*Common Name:**	Calyxin L
IUPAC Name:	(E)-1-[(2R,4R)-5-hydroxy-4-[(2S)-2-hydroxy-4-(4-hydroxyphenyl)butyl]-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-chromen-8-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:	Calyxin L
Standard InCHIKey:	WVMXLWIYDSSCRW-KBYRMXMQSA-N
Standard InCHI:	InChI=1S/C35H34O8/c1-42-32-20-30(41)33-24(18-28(39)14-6-21-2-10-25(36)11-3-21)19-31(23-8-15-27(38)16-9-23)43-35(33)34(32)29(40)17-7-22-4-12-26(37)13-5-22/h2-5,7-13,15-17,20,24,28,31,36-39,41H,6,14,18-19H2,1H3/b17-7+/t24-,28+,31-/m1/s1
SMILES:	COc1cc(c2[C@H](C[C@H](CCc3ccc(cc3)O)O)C[C@H](c3ccc(cc3)O)Oc2c1C(=O)/C=C/c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448657
PubChem CID:	10722001
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	44.3	uM	PMID[545542]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	28.2	uM	PMID[545542]

☑ 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 NPC15815 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	398
0.1-0.2	1484
0.2-0.3	3375
0.3-0.4	8668
0.4-0.5	10229
0.5-0.6	3617
0.6-0.7	5836
0.7-0.8	5359
0.8-0.85	2339
0.85-0.9	996
0.9-0.95	352
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC257166
0.9868	High Similarity	NPC51247
0.9803	High Similarity	NPC226462
0.9803	High Similarity	NPC195136
0.9803	High Similarity	NPC98023
0.9801	High Similarity	NPC1796
0.9801	High Similarity	NPC208258
0.98	High Similarity	NPC79375
0.98	High Similarity	NPC37253
0.9737	High Similarity	NPC105584
0.9733	High Similarity	NPC121568
0.9673	High Similarity	NPC42965
0.9673	High Similarity	NPC121647
0.9671	High Similarity	NPC475184
0.9667	High Similarity	NPC43345
0.96	High Similarity	NPC476552
0.96	High Similarity	NPC476553
0.96	High Similarity	NPC178484
0.96	High Similarity	NPC476551
0.9548	High Similarity	NPC473012
0.9542	High Similarity	NPC318527
0.9542	High Similarity	NPC322459
0.9542	High Similarity	NPC324358
0.9542	High Similarity	NPC323627
0.9536	High Similarity	NPC78324
0.9536	High Similarity	NPC39154
0.9536	High Similarity	NPC208011
0.9536	High Similarity	NPC115601
0.949	High Similarity	NPC251336
0.9487	High Similarity	NPC473009
0.9484	High Similarity	NPC312273
0.9484	High Similarity	NPC301256
0.9477	High Similarity	NPC32867
0.9477	High Similarity	NPC69531
0.9477	High Similarity	NPC56049
0.9477	High Similarity	NPC54830
0.9474	High Similarity	NPC324447
0.9467	High Similarity	NPC3642
0.9427	High Similarity	NPC473010
0.9416	High Similarity	NPC271741
0.9416	High Similarity	NPC287789
0.9412	High Similarity	NPC134171
0.9412	High Similarity	NPC300668
0.9412	High Similarity	NPC182555
0.9412	High Similarity	NPC66441
0.9408	High Similarity	NPC174086
0.94	High Similarity	NPC152233
0.94	High Similarity	NPC122894
0.9355	High Similarity	NPC295090
0.9355	High Similarity	NPC51760
0.9351	High Similarity	NPC61112
0.9351	High Similarity	NPC198489
0.9351	High Similarity	NPC309648
0.9338	High Similarity	NPC132345
0.9333	High Similarity	NPC475348
0.9333	High Similarity	NPC261271
0.9286	High Similarity	NPC158027
0.9286	High Similarity	NPC215203
0.9286	High Similarity	NPC14606
0.9286	High Similarity	NPC100049
0.9286	High Similarity	NPC159707
0.9286	High Similarity	NPC205026
0.9286	High Similarity	NPC258474
0.9286	High Similarity	NPC52611
0.9286	High Similarity	NPC121649
0.9286	High Similarity	NPC248739
0.9286	High Similarity	NPC265624
0.9286	High Similarity	NPC201227
0.9286	High Similarity	NPC186227
0.9286	High Similarity	NPC150908
0.9267	High Similarity	NPC470131
0.9267	High Similarity	NPC228779
0.9267	High Similarity	NPC109183
0.9267	High Similarity	NPC470134
0.9267	High Similarity	NPC470133
0.9267	High Similarity	NPC473078
0.9267	High Similarity	NPC470132
0.9255	High Similarity	NPC477529
0.9241	High Similarity	NPC63438
0.9231	High Similarity	NPC123544
0.9231	High Similarity	NPC90497
0.9221	High Similarity	NPC290830
0.9221	High Similarity	NPC71061
0.9221	High Similarity	NPC194593
0.9221	High Similarity	NPC303485
0.9221	High Similarity	NPC72425
0.9216	High Similarity	NPC316960
0.9216	High Similarity	NPC148945
0.9216	High Similarity	NPC204561
0.9216	High Similarity	NPC317715
0.9216	High Similarity	NPC78835
0.9216	High Similarity	NPC309512
0.9211	High Similarity	NPC473016
0.92	High Similarity	NPC471523
0.92	High Similarity	NPC473014
0.92	High Similarity	NPC271288
0.92	High Similarity	NPC473015
0.92	High Similarity	NPC39045
0.92	High Similarity	NPC470135
0.92	High Similarity	NPC471524
0.92	High Similarity	NPC473013
0.92	High Similarity	NPC282957
0.92	High Similarity	NPC235217
0.92	High Similarity	NPC471473
0.92	High Similarity	NPC470136
0.92	High Similarity	NPC194949
0.92	High Similarity	NPC236766
0.92	High Similarity	NPC197252
0.9177	High Similarity	NPC473011
0.9145	High Similarity	NPC160821
0.9145	High Similarity	NPC39195
0.9145	High Similarity	NPC145467
0.9145	High Similarity	NPC132592
0.9139	High Similarity	NPC127059
0.9139	High Similarity	NPC472629
0.9139	High Similarity	NPC477955
0.9139	High Similarity	NPC285630
0.9133	High Similarity	NPC185276
0.9133	High Similarity	NPC143896
0.9133	High Similarity	NPC310130
0.9133	High Similarity	NPC81697
0.9133	High Similarity	NPC150408
0.9133	High Similarity	NPC91560
0.9133	High Similarity	NPC107177
0.9133	High Similarity	NPC125894
0.9133	High Similarity	NPC75049
0.9133	High Similarity	NPC175504
0.9133	High Similarity	NPC68104
0.9133	High Similarity	NPC223812
0.9133	High Similarity	NPC85162
0.9133	High Similarity	NPC39329
0.9133	High Similarity	NPC169591
0.9133	High Similarity	NPC257097
0.9133	High Similarity	NPC221432
0.9133	High Similarity	NPC278249
0.9133	High Similarity	NPC77794
0.9133	High Similarity	NPC164980
0.9133	High Similarity	NPC149026
0.9119	High Similarity	NPC38591
0.9114	High Similarity	NPC175513
0.9114	High Similarity	NPC18380
0.9114	High Similarity	NPC97812
0.9108	High Similarity	NPC195167
0.9108	High Similarity	NPC55443
0.9108	High Similarity	NPC18699
0.9103	High Similarity	NPC78492
0.9103	High Similarity	NPC208152
0.9091	High Similarity	NPC138299
0.9091	High Similarity	NPC67322
0.9091	High Similarity	NPC222713
0.9091	High Similarity	NPC111112
0.9085	High Similarity	NPC291746
0.9085	High Similarity	NPC288840
0.908	High Similarity	NPC168789
0.9079	High Similarity	NPC283234
0.9079	High Similarity	NPC308200
0.9079	High Similarity	NPC10990
0.9079	High Similarity	NPC296998
0.9079	High Similarity	NPC23728
0.9079	High Similarity	NPC110303
0.9079	High Similarity	NPC473077
0.9079	High Similarity	NPC300988
0.9073	High Similarity	NPC87486
0.9073	High Similarity	NPC209040
0.9073	High Similarity	NPC470890
0.9073	High Similarity	NPC131579
0.9073	High Similarity	NPC124780
0.9073	High Similarity	NPC131568
0.9067	High Similarity	NPC324436
0.9067	High Similarity	NPC194432
0.9067	High Similarity	NPC223500
0.9067	High Similarity	NPC66515
0.9067	High Similarity	NPC328164
0.9067	High Similarity	NPC182852
0.9067	High Similarity	NPC306829
0.9067	High Similarity	NPC228504
0.9067	High Similarity	NPC125855
0.9067	High Similarity	NPC296917
0.9067	High Similarity	NPC202981
0.9067	High Similarity	NPC64915
0.9067	High Similarity	NPC324134
0.9067	High Similarity	NPC40833
0.9067	High Similarity	NPC166934
0.9067	High Similarity	NPC177354
0.9067	High Similarity	NPC161506
0.9067	High Similarity	NPC148757
0.9067	High Similarity	NPC37496
0.9067	High Similarity	NPC167624
0.9067	High Similarity	NPC107572
0.9067	High Similarity	NPC1089
0.9067	High Similarity	NPC227579
0.9067	High Similarity	NPC78
0.9067	High Similarity	NPC166482
0.9067	High Similarity	NPC220998
0.9067	High Similarity	NPC76338
0.9067	High Similarity	NPC76372
0.9067	High Similarity	NPC32739
0.9067	High Similarity	NPC10937
0.9067	High Similarity	NPC265040
0.9062	High Similarity	NPC469664

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 NPC15815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	952
0.2-0.3	1490
0.3-0.4	2570
0.4-0.5	2015
0.5-0.6	1141
0.6-0.7	416
0.7-0.8	166
0.8-0.85	32
0.85-0.9	15
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD8443	Clinical (unspecified phase)
0.9182	High Similarity	NPD7852	Clinical (unspecified phase)
0.8994	High Similarity	NPD6959	Discontinued
0.8981	High Similarity	NPD7768	Phase 2
0.8968	High Similarity	NPD7411	Suspended
0.8947	High Similarity	NPD7410	Clinical (unspecified phase)
0.8903	High Similarity	NPD4380	Phase 2
0.8854	High Similarity	NPD7819	Suspended
0.8805	High Similarity	NPD7075	Discontinued
0.88	High Similarity	NPD1549	Phase 2
0.8733	High Similarity	NPD1550	Clinical (unspecified phase)
0.8733	High Similarity	NPD1552	Clinical (unspecified phase)
0.8701	High Similarity	NPD4378	Clinical (unspecified phase)
0.8667	High Similarity	NPD7804	Clinical (unspecified phase)
0.8616	High Similarity	NPD7096	Clinical (unspecified phase)
0.8616	High Similarity	NPD2393	Clinical (unspecified phase)
0.8598	High Similarity	NPD6166	Phase 2
0.8598	High Similarity	NPD6168	Clinical (unspecified phase)
0.8598	High Similarity	NPD6167	Clinical (unspecified phase)
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8543	High Similarity	NPD2796	Approved
0.8477	Intermediate Similarity	NPD1510	Phase 2
0.8438	Intermediate Similarity	NPD6801	Discontinued
0.8344	Intermediate Similarity	NPD3749	Approved
0.8333	Intermediate Similarity	NPD1240	Approved
0.8323	Intermediate Similarity	NPD1934	Approved
0.8284	Intermediate Similarity	NPD7074	Phase 3
0.8258	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5494	Approved
0.8235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7054	Approved
0.8224	Intermediate Similarity	NPD1607	Approved
0.82	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD8312	Approved
0.8198	Intermediate Similarity	NPD8313	Approved
0.8176	Intermediate Similarity	NPD7472	Approved
0.8171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD7808	Phase 3
0.8118	Intermediate Similarity	NPD5844	Phase 1
0.8107	Intermediate Similarity	NPD7473	Discontinued
0.8089	Intermediate Similarity	NPD3750	Approved
0.8081	Intermediate Similarity	NPD6559	Discontinued
0.8081	Intermediate Similarity	NPD7251	Discontinued
0.8067	Intermediate Similarity	NPD4908	Phase 1
0.805	Intermediate Similarity	NPD6799	Approved
0.805	Intermediate Similarity	NPD7390	Discontinued
0.8023	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD5403	Approved
0.7987	Intermediate Similarity	NPD6651	Approved
0.7978	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7953	Intermediate Similarity	NPD3818	Discontinued
0.7952	Intermediate Similarity	NPD3882	Suspended
0.7939	Intermediate Similarity	NPD8455	Phase 2
0.7939	Intermediate Similarity	NPD2801	Approved
0.7937	Intermediate Similarity	NPD1511	Approved
0.7931	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6232	Discontinued
0.7911	Intermediate Similarity	NPD2800	Approved
0.7901	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5401	Approved
0.7885	Intermediate Similarity	NPD2799	Discontinued
0.7848	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1512	Approved
0.7834	Intermediate Similarity	NPD1551	Phase 2
0.7816	Intermediate Similarity	NPD5953	Discontinued
0.7805	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7458	Discontinued
0.779	Intermediate Similarity	NPD4363	Phase 3
0.779	Intermediate Similarity	NPD4360	Phase 2
0.7785	Intermediate Similarity	NPD2344	Approved
0.7784	Intermediate Similarity	NPD3817	Phase 2
0.7784	Intermediate Similarity	NPD5402	Approved
0.7778	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3748	Approved
0.7765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7727	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD6099	Approved
0.7722	Intermediate Similarity	NPD2935	Discontinued
0.7701	Intermediate Similarity	NPD7286	Phase 2
0.7697	Intermediate Similarity	NPD3226	Approved
0.7688	Intermediate Similarity	NPD1243	Approved
0.7683	Intermediate Similarity	NPD920	Approved
0.7669	Intermediate Similarity	NPD2533	Approved
0.7669	Intermediate Similarity	NPD2534	Approved
0.7669	Intermediate Similarity	NPD2532	Approved
0.7658	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7003	Approved
0.764	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD8151	Discontinued
0.7606	Intermediate Similarity	NPD7870	Phase 2
0.7606	Intermediate Similarity	NPD7871	Phase 2
0.76	Intermediate Similarity	NPD1610	Phase 2
0.76	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6832	Phase 2
0.7593	Intermediate Similarity	NPD2309	Approved
0.758	Intermediate Similarity	NPD5124	Phase 1
0.758	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8150	Discontinued
0.7553	Intermediate Similarity	NPD7696	Phase 3
0.7553	Intermediate Similarity	NPD7698	Approved
0.7553	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7468	Intermediate Similarity	NPD2798	Approved
0.746	Intermediate Similarity	NPD7435	Discontinued
0.7459	Intermediate Similarity	NPD4361	Phase 2
0.7459	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7443	Intermediate Similarity	NPD3751	Discontinued
0.7438	Intermediate Similarity	NPD7033	Discontinued
0.7435	Intermediate Similarity	NPD7584	Approved
0.7414	Intermediate Similarity	NPD7229	Phase 3
0.7414	Intermediate Similarity	NPD3787	Discontinued
0.7412	Intermediate Similarity	NPD1465	Phase 2
0.741	Intermediate Similarity	NPD6273	Approved
0.7403	Intermediate Similarity	NPD1203	Approved
0.7396	Intermediate Similarity	NPD7701	Phase 2
0.7394	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3268	Approved
0.7377	Intermediate Similarity	NPD4287	Approved
0.7371	Intermediate Similarity	NPD7801	Approved
0.7371	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7783	Phase 2
0.7365	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8434	Phase 2
0.7356	Intermediate Similarity	NPD7199	Phase 2
0.7353	Intermediate Similarity	NPD7577	Discontinued
0.7345	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7177	Discontinued
0.7341	Intermediate Similarity	NPD919	Approved
0.732	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7874	Approved
0.7316	Intermediate Similarity	NPD6823	Phase 2
0.731	Intermediate Similarity	NPD5761	Phase 2
0.731	Intermediate Similarity	NPD5760	Phase 2
0.7308	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD943	Approved
0.729	Intermediate Similarity	NPD2797	Approved
0.7287	Intermediate Similarity	NPD7700	Phase 2
0.7287	Intermediate Similarity	NPD7699	Phase 2
0.7278	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1247	Approved
0.7251	Intermediate Similarity	NPD6844	Discontinued
0.7247	Intermediate Similarity	NPD7228	Approved
0.7246	Intermediate Similarity	NPD7447	Phase 1
0.7246	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8320	Phase 1
0.724	Intermediate Similarity	NPD8319	Approved
0.7239	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7219	Intermediate Similarity	NPD6535	Approved
0.7219	Intermediate Similarity	NPD6534	Approved
0.7216	Intermediate Similarity	NPD5710	Approved
0.7216	Intermediate Similarity	NPD5711	Approved
0.7215	Intermediate Similarity	NPD4625	Phase 3
0.7208	Intermediate Similarity	NPD9717	Approved
0.7188	Intermediate Similarity	NPD1613	Approved
0.7188	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7213	Phase 3
0.7186	Intermediate Similarity	NPD7212	Phase 2
0.7175	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD6798	Discontinued
0.7168	Intermediate Similarity	NPD4288	Approved
0.7167	Intermediate Similarity	NPD1729	Discontinued
0.716	Intermediate Similarity	NPD7097	Phase 1
0.7159	Intermediate Similarity	NPD8127	Discontinued
0.7151	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4966	Approved
0.7117	Intermediate Similarity	NPD4308	Phase 3
0.7097	Intermediate Similarity	NPD1608	Approved
0.7097	Intermediate Similarity	NPD3972	Approved
0.7093	Intermediate Similarity	NPD5890	Approved
0.7093	Intermediate Similarity	NPD5889	Approved
0.7089	Intermediate Similarity	NPD2861	Phase 2
0.7088	Intermediate Similarity	NPD7685	Pre-registration
0.7088	Intermediate Similarity	NPD6104	Discontinued

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