NPASS Compound

Structure

CID98023 OpenBabel06191715432D 51 57 0 0 1 0 0 0 0 0999 V2000 -4.1136 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -6.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4682 -6.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9363 0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1136 2.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -4.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2909 0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7591 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9363 0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4682 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -7.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4682 -7.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7591 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9363 2.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5818 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7591 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2909 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4682 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -4.2750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4682 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4682 -1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -5.7000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1136 1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9363 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -7.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7591 2.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5818 0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2909 0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -3.3250 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.9000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6454 0.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6454 -1.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4682 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8227 -1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -1.4250 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6454 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -1.9000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8227 -0.4750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8227 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -8.5500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5818 2.8500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4045 1.4250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1136 1.4250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8227 1.4250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6454 -2.8500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2909 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6454 -2.8500 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 49 1 0 0 0 0 2 12 1 0 0 0 0 2 24 2 0 0 0 0 3 13 2 0 0 0 0 3 24 1 0 0 0 0 4 14 1 0 0 0 0 4 25 2 0 0 0 0 5 15 2 0 0 0 0 5 25 1 0 0 0 0 6 20 1 0 0 0 0 6 24 1 0 0 0 0 7 21 2 0 0 0 0 7 25 1 0 0 0 0 8 16 1 0 0 0 0 8 26 2 0 0 0 0 9 17 2 0 0 0 0 9 26 1 0 0 0 0 10 18 1 0 0 0 0 10 27 2 0 0 0 0 11 19 2 0 0 0 0 11 27 1 0 0 0 0 12 28 2 0 0 0 0 13 28 1 0 0 0 0 14 29 2 0 0 0 0 15 29 1 0 0 0 0 16 30 2 0 0 0 0 17 30 1 0 0 0 0 18 31 2 0 0 0 0 19 31 1 0 0 0 0 21 34 1 0 0 0 0 22 32 1 0 0 0 0 23 35 2 0 0 0 0 23 36 1 0 0 0 0 26 40 1 0 0 0 0 27 41 1 0 0 0 0 28 43 1 0 0 0 0 29 44 1 0 0 0 0 30 45 1 0 0 0 0 31 46 1 0 0 0 0 32 20 1 1 0 0 0 32 50 1 0 0 0 0 33 22 1 1 0 0 0 33 37 1 0 0 0 0 33 38 1 0 0 0 0 34 39 1 0 0 0 0 34 47 2 0 0 0 0 35 37 1 0 0 0 0 35 48 1 0 0 0 0 36 39 2 0 0 0 0 36 49 1 0 0 0 0 37 42 2 0 0 0 0 38 40 1 0 0 0 0 38 41 1 0 0 0 0 39 42 1 0 0 0 0 40 50 1 0 0 0 0 41 51 1 0 0 0 0 42 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	686.25
Volume:	709.385
LogP:	6.336
LogD:	4.458
LogS:	-4.043
# Rotatable Bonds:	9
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.077
Synthetic Accessibility Score:	4.515
Fsp3:	0.214
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.166
MDCK Permeability:	7.90837930253474e-06
Pgp-inhibitor:	0.32
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.227
20% Bioavailability (F20%):	0.893
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	101.29462432861328%
Volume Distribution (VD):	0.21
Pgp-substrate:	1.0784540176391602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.894
CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.492
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.711
CYP3A4-substrate:	0.473

ADMET: Excretion

Clearance (CL):	10.936
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.289
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.512
Rat Oral Acute Toxicity:	0.724
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.967
Carcinogencity:	0.415
Eye Corrosion:	0.003
Eye Irritation:	0.808
Respiratory Toxicity:	0.174

Download Data

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

Natural Product: NPC98023

Natural Product ID:	NPC98023
*Common Name:**	Calyxin I
IUPAC Name:	(E)-1-[(2S,4S,4aS,5R,10bR)-10-hydroxy-4,5-bis(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethyl]-8-methoxy-1,2,4,4a,5,10b-hexahydropyrano[3,4-c]chromen-7-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:	Calyxin I
Standard InCHIKey:	UJEBJUQQVRWYAG-SOFNOPICSA-N
Standard InCHI:	InChI=1S/C42H38O9/c1-49-36-23-35(48)37-33-22-32(20-6-24-2-12-28(43)13-3-24)50-40(26-8-16-30(45)17-9-26)38(33)41(27-10-18-31(46)19-11-27)51-42(37)39(36)34(47)21-7-25-4-14-29(44)15-5-25/h2-5,7-19,21,23,32-33,38,40-41,43-46,48H,6,20,22H2,1H3/b21-7+/t32-,33-,38-,40+,41-/m0/s1
SMILES:	COc1cc(c2[C@@H]3C[C@H](CCc4ccc(cc4)O)O[C@H](c4ccc(cc4)O)[C@H]3[C@H](c3ccc(cc3)O)Oc2c1C(=O)/C=C/c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455049
PubChem CID:	10327269
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	=	9.08	uM	PMID[504332]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.39	uM	PMID[504332]

☑ 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 NPC98023 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	402
0.1-0.2	1489
0.2-0.3	3298
0.3-0.4	8540
0.4-0.5	10415
0.5-0.6	3797
0.6-0.7	5889
0.7-0.8	5252
0.8-0.85	2425
0.85-0.9	917
0.9-0.95	248
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC226462
0.9868	High Similarity	NPC42965
0.9868	High Similarity	NPC1796
0.9803	High Similarity	NPC15815
0.9803	High Similarity	NPC51247
0.9739	High Similarity	NPC195136
0.9737	High Similarity	NPC208258
0.9737	High Similarity	NPC257166
0.9735	High Similarity	NPC37253
0.9735	High Similarity	NPC79375
0.9673	High Similarity	NPC105584
0.9669	High Similarity	NPC121568
0.961	High Similarity	NPC121647
0.9608	High Similarity	NPC475184
0.9603	High Similarity	NPC39154
0.9603	High Similarity	NPC208011
0.9603	High Similarity	NPC78324
0.9603	High Similarity	NPC115601
0.9542	High Similarity	NPC69531
0.9536	High Similarity	NPC178484
0.949	High Similarity	NPC473010
0.9487	High Similarity	NPC473012
0.9481	High Similarity	NPC322459
0.9481	High Similarity	NPC324358
0.9481	High Similarity	NPC323627
0.9481	High Similarity	NPC318527
0.9481	High Similarity	NPC287789
0.9481	High Similarity	NPC271741
0.9477	High Similarity	NPC134171
0.9477	High Similarity	NPC300668
0.9474	High Similarity	NPC43345
0.943	High Similarity	NPC251336
0.9427	High Similarity	NPC473009
0.9423	High Similarity	NPC301256
0.9423	High Similarity	NPC312273
0.9419	High Similarity	NPC51760
0.9416	High Similarity	NPC198489
0.9416	High Similarity	NPC61112
0.9416	High Similarity	NPC309648
0.9416	High Similarity	NPC32867
0.9416	High Similarity	NPC56049
0.9416	High Similarity	NPC54830
0.9412	High Similarity	NPC324447
0.9408	High Similarity	NPC476551
0.9408	High Similarity	NPC476553
0.9408	High Similarity	NPC476552
0.9404	High Similarity	NPC132345
0.9404	High Similarity	NPC3642
0.9351	High Similarity	NPC258474
0.9351	High Similarity	NPC201227
0.9351	High Similarity	NPC182555
0.9351	High Similarity	NPC66441
0.9346	High Similarity	NPC174086
0.9338	High Similarity	NPC152233
0.9338	High Similarity	NPC122894
0.9295	High Similarity	NPC295090
0.9276	High Similarity	NPC473016
0.9272	High Similarity	NPC475348
0.9272	High Similarity	NPC261271
0.9226	High Similarity	NPC150908
0.9226	High Similarity	NPC205026
0.9226	High Similarity	NPC158027
0.9226	High Similarity	NPC215203
0.9226	High Similarity	NPC52611
0.9226	High Similarity	NPC100049
0.9226	High Similarity	NPC121649
0.9226	High Similarity	NPC248739
0.9226	High Similarity	NPC265624
0.9226	High Similarity	NPC14606
0.9226	High Similarity	NPC159707
0.9226	High Similarity	NPC186227
0.9205	High Similarity	NPC470133
0.9205	High Similarity	NPC473078
0.9205	High Similarity	NPC470131
0.9205	High Similarity	NPC470132
0.9205	High Similarity	NPC228779
0.9205	High Similarity	NPC109183
0.9205	High Similarity	NPC470134
0.9198	High Similarity	NPC477529
0.9182	High Similarity	NPC63438
0.9177	High Similarity	NPC175513
0.9177	High Similarity	NPC18380
0.9172	High Similarity	NPC90497
0.9172	High Similarity	NPC195167
0.9161	High Similarity	NPC303485
0.9161	High Similarity	NPC71061
0.9161	High Similarity	NPC290830
0.9161	High Similarity	NPC72425
0.9161	High Similarity	NPC194593
0.9156	High Similarity	NPC309512
0.9156	High Similarity	NPC204561
0.9156	High Similarity	NPC148945
0.9156	High Similarity	NPC317715
0.9156	High Similarity	NPC78835
0.9156	High Similarity	NPC316960
0.9139	High Similarity	NPC471473
0.9139	High Similarity	NPC470136
0.9139	High Similarity	NPC271288
0.9139	High Similarity	NPC473013
0.9139	High Similarity	NPC471523
0.9139	High Similarity	NPC282957
0.9139	High Similarity	NPC39045
0.9139	High Similarity	NPC471524
0.9139	High Similarity	NPC235217
0.9139	High Similarity	NPC197252
0.9139	High Similarity	NPC236766
0.9139	High Similarity	NPC473015
0.9139	High Similarity	NPC470135
0.9139	High Similarity	NPC473014
0.9139	High Similarity	NPC194949
0.9119	High Similarity	NPC473011
0.9119	High Similarity	NPC15374
0.9114	High Similarity	NPC184326
0.9114	High Similarity	NPC292863
0.9085	High Similarity	NPC145467
0.9085	High Similarity	NPC132592
0.9085	High Similarity	NPC160821
0.9085	High Similarity	NPC39195
0.9079	High Similarity	NPC477955
0.9079	High Similarity	NPC285630
0.9079	High Similarity	NPC127059
0.9073	High Similarity	NPC150408
0.9073	High Similarity	NPC185276
0.9073	High Similarity	NPC75049
0.9073	High Similarity	NPC223812
0.9073	High Similarity	NPC221432
0.9073	High Similarity	NPC81697
0.9073	High Similarity	NPC39329
0.9073	High Similarity	NPC164980
0.9073	High Similarity	NPC143896
0.9073	High Similarity	NPC125894
0.9073	High Similarity	NPC85162
0.9073	High Similarity	NPC91560
0.9073	High Similarity	NPC77794
0.9073	High Similarity	NPC278249
0.9073	High Similarity	NPC107177
0.9073	High Similarity	NPC257097
0.9073	High Similarity	NPC149026
0.9073	High Similarity	NPC169591
0.9073	High Similarity	NPC175504
0.9073	High Similarity	NPC68104
0.9073	High Similarity	NPC310130
0.9068	High Similarity	NPC224851
0.9062	High Similarity	NPC38591
0.9057	High Similarity	NPC137232
0.9057	High Similarity	NPC114652
0.9051	High Similarity	NPC55443
0.9051	High Similarity	NPC18699
0.9051	High Similarity	NPC123544
0.9032	High Similarity	NPC209142
0.9032	High Similarity	NPC67322
0.9032	High Similarity	NPC138299
0.9032	High Similarity	NPC222713
0.9032	High Similarity	NPC312549
0.9032	High Similarity	NPC111112
0.9026	High Similarity	NPC291746
0.9026	High Similarity	NPC288840
0.9024	High Similarity	NPC168789
0.902	High Similarity	NPC308200
0.902	High Similarity	NPC283234
0.902	High Similarity	NPC473077
0.902	High Similarity	NPC110303
0.902	High Similarity	NPC296998
0.902	High Similarity	NPC10990
0.902	High Similarity	NPC300988
0.902	High Similarity	NPC23728
0.9013	High Similarity	NPC209040
0.9013	High Similarity	NPC131579
0.9013	High Similarity	NPC131568
0.9007	High Similarity	NPC76372
0.9007	High Similarity	NPC227579
0.9007	High Similarity	NPC324436
0.9007	High Similarity	NPC194432
0.9007	High Similarity	NPC223500
0.9007	High Similarity	NPC66515
0.9007	High Similarity	NPC167624
0.9007	High Similarity	NPC182852
0.9007	High Similarity	NPC328164
0.9007	High Similarity	NPC306829
0.9007	High Similarity	NPC177354
0.9007	High Similarity	NPC40833
0.9007	High Similarity	NPC202981
0.9007	High Similarity	NPC64915
0.9007	High Similarity	NPC166934
0.9007	High Similarity	NPC125855
0.9007	High Similarity	NPC296917
0.9007	High Similarity	NPC324134
0.9007	High Similarity	NPC148757
0.9007	High Similarity	NPC161506
0.9007	High Similarity	NPC37496
0.9007	High Similarity	NPC78
0.9007	High Similarity	NPC1089
0.9007	High Similarity	NPC166482
0.9007	High Similarity	NPC228504
0.9007	High Similarity	NPC107572
0.9007	High Similarity	NPC10937
0.9007	High Similarity	NPC220998
0.9007	High Similarity	NPC265040
0.9007	High Similarity	NPC76338
0.9007	High Similarity	NPC32739

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 NPC98023 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	909
0.2-0.3	1489
0.3-0.4	2554
0.4-0.5	2089
0.5-0.6	1149
0.6-0.7	415
0.7-0.8	150
0.8-0.85	33
0.85-0.9	12
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9477	High Similarity	NPD8443	Clinical (unspecified phase)
0.9125	High Similarity	NPD7852	Clinical (unspecified phase)
0.9057	High Similarity	NPD6959	Discontinued
0.8924	High Similarity	NPD7768	Phase 2
0.891	High Similarity	NPD7411	Suspended
0.8889	High Similarity	NPD7410	Clinical (unspecified phase)
0.8797	High Similarity	NPD7819	Suspended
0.875	High Similarity	NPD7075	Discontinued
0.8742	High Similarity	NPD1549	Phase 2
0.8726	High Similarity	NPD4380	Phase 2
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8614	High Similarity	NPD7804	Clinical (unspecified phase)
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8545	High Similarity	NPD6166	Phase 2
0.8545	High Similarity	NPD6168	Clinical (unspecified phase)
0.8545	High Similarity	NPD6167	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD2796	Approved
0.8421	Intermediate Similarity	NPD1510	Phase 2
0.8405	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD5494	Approved
0.8293	Intermediate Similarity	NPD3749	Approved
0.8278	Intermediate Similarity	NPD1240	Approved
0.8272	Intermediate Similarity	NPD1934	Approved
0.8272	Intermediate Similarity	NPD6801	Discontinued
0.8256	Intermediate Similarity	NPD8312	Approved
0.8256	Intermediate Similarity	NPD8313	Approved
0.8235	Intermediate Similarity	NPD7074	Phase 3
0.8205	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7054	Approved
0.817	Intermediate Similarity	NPD1607	Approved
0.8146	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7472	Approved
0.8121	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7390	Discontinued
0.8092	Intermediate Similarity	NPD7808	Phase 3
0.8059	Intermediate Similarity	NPD7473	Discontinued
0.8038	Intermediate Similarity	NPD3750	Approved
0.8035	Intermediate Similarity	NPD7251	Discontinued
0.8013	Intermediate Similarity	NPD4908	Phase 1
0.8	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD6797	Phase 2
0.7965	Intermediate Similarity	NPD5844	Phase 1
0.7935	Intermediate Similarity	NPD6651	Approved
0.7931	Intermediate Similarity	NPD6559	Discontinued
0.7927	Intermediate Similarity	NPD6599	Discontinued
0.7904	Intermediate Similarity	NPD3882	Suspended
0.7892	Intermediate Similarity	NPD2801	Approved
0.7892	Intermediate Similarity	NPD8455	Phase 2
0.7888	Intermediate Similarity	NPD1511	Approved
0.7882	Intermediate Similarity	NPD6232	Discontinued
0.7866	Intermediate Similarity	NPD7458	Discontinued
0.7862	Intermediate Similarity	NPD2800	Approved
0.7853	Intermediate Similarity	NPD5403	Approved
0.7834	Intermediate Similarity	NPD2799	Discontinued
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD3818	Discontinued
0.7799	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1512	Approved
0.7785	Intermediate Similarity	NPD1551	Phase 2
0.7784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.776	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3817	Phase 2
0.7736	Intermediate Similarity	NPD2344	Approved
0.773	Intermediate Similarity	NPD5401	Approved
0.7722	Intermediate Similarity	NPD3748	Approved
0.7702	Intermediate Similarity	NPD7003	Approved
0.7684	Intermediate Similarity	NPD8151	Discontinued
0.7673	Intermediate Similarity	NPD6100	Approved
0.7673	Intermediate Similarity	NPD2935	Discontinued
0.7673	Intermediate Similarity	NPD6099	Approved
0.7657	Intermediate Similarity	NPD7286	Phase 2
0.7651	Intermediate Similarity	NPD3226	Approved
0.7651	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD4363	Phase 3
0.765	Intermediate Similarity	NPD4360	Phase 2
0.764	Intermediate Similarity	NPD1243	Approved
0.7636	Intermediate Similarity	NPD920	Approved
0.7633	Intermediate Similarity	NPD5402	Approved
0.7622	Intermediate Similarity	NPD2533	Approved
0.7622	Intermediate Similarity	NPD2534	Approved
0.7622	Intermediate Similarity	NPD2532	Approved
0.7622	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4628	Phase 3
0.7584	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7871	Phase 2
0.7566	Intermediate Similarity	NPD7870	Phase 2
0.755	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1610	Phase 2
0.7548	Intermediate Similarity	NPD6832	Phase 2
0.7546	Intermediate Similarity	NPD2309	Approved
0.7515	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7697	Approved
0.7513	Intermediate Similarity	NPD7698	Approved
0.7513	Intermediate Similarity	NPD7696	Phase 3
0.7485	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1465	Phase 2
0.7456	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5408	Approved
0.7453	Intermediate Similarity	NPD5406	Approved
0.7453	Intermediate Similarity	NPD5404	Approved
0.7453	Intermediate Similarity	NPD5405	Approved
0.7452	Intermediate Similarity	NPD2313	Discontinued
0.7429	Intermediate Similarity	NPD3926	Phase 2
0.7421	Intermediate Similarity	NPD5124	Phase 1
0.7421	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2798	Approved
0.7418	Intermediate Similarity	NPD8150	Discontinued
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7358	Intermediate Similarity	NPD7701	Phase 2
0.7355	Intermediate Similarity	NPD1203	Approved
0.7354	Intermediate Similarity	NPD6776	Approved
0.7354	Intermediate Similarity	NPD6778	Approved
0.7354	Intermediate Similarity	NPD6779	Approved
0.7354	Intermediate Similarity	NPD6782	Approved
0.7354	Intermediate Similarity	NPD6781	Approved
0.7354	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6777	Approved
0.7354	Intermediate Similarity	NPD6780	Approved
0.7342	Intermediate Similarity	NPD3268	Approved
0.7337	Intermediate Similarity	NPD4287	Approved
0.7333	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7783	Phase 2
0.733	Intermediate Similarity	NPD7435	Discontinued
0.7326	Intermediate Similarity	NPD4361	Phase 2
0.7326	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7577	Discontinued
0.7306	Intermediate Similarity	NPD7584	Approved
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7177	Discontinued
0.7299	Intermediate Similarity	NPD919	Approved
0.7284	Intermediate Similarity	NPD7033	Discontinued
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6273	Approved
0.725	Intermediate Similarity	NPD943	Approved
0.7249	Intermediate Similarity	NPD7700	Phase 2
0.7249	Intermediate Similarity	NPD7699	Phase 2
0.7245	Intermediate Similarity	NPD7801	Approved
0.7244	Intermediate Similarity	NPD2797	Approved
0.7228	Intermediate Similarity	NPD8434	Phase 2
0.7216	Intermediate Similarity	NPD1247	Approved
0.7216	Intermediate Similarity	NPD7199	Phase 2
0.7207	Intermediate Similarity	NPD7228	Approved
0.7202	Intermediate Similarity	NPD7447	Phase 1
0.7202	Intermediate Similarity	NPD8320	Phase 1
0.7202	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8319	Approved
0.7195	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6823	Phase 2
0.7175	Intermediate Similarity	NPD5711	Approved
0.7175	Intermediate Similarity	NPD5710	Approved
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.717	Intermediate Similarity	NPD4625	Phase 3
0.7168	Intermediate Similarity	NPD5761	Phase 2
0.7168	Intermediate Similarity	NPD5760	Phase 2
0.7161	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD7213	Phase 3
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1729	Discontinued
0.7126	Intermediate Similarity	NPD4288	Approved
0.7125	Intermediate Similarity	NPD3764	Approved
0.7125	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6798	Discontinued
0.7117	Intermediate Similarity	NPD7097	Phase 1
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.709	Intermediate Similarity	NPD6534	Approved
0.709	Intermediate Similarity	NPD6535	Approved
0.7073	Intermediate Similarity	NPD4308	Phase 3
0.7066	Intermediate Similarity	NPD8166	Discontinued
0.7052	Intermediate Similarity	NPD5890	Approved
0.7052	Intermediate Similarity	NPD5889	Approved
0.7051	Intermediate Similarity	NPD1608	Approved
0.7051	Intermediate Similarity	NPD3972	Approved
0.7049	Intermediate Similarity	NPD6104	Discontinued
0.7044	Intermediate Similarity	NPD2861	Phase 2
0.7037	Intermediate Similarity	NPD1613	Approved
0.7037	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2296	Approved
0.7025	Intermediate Similarity	NPD3267	Approved
0.7025	Intermediate Similarity	NPD3266	Approved
0.7025	Intermediate Similarity	NPD1470	Approved
0.7022	Intermediate Similarity	NPD8127	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