NPASS Compound

Structure

NPC473250 OpenBabel07101719252D 45 50 0 0 1 0 0 0 0 0999 V2000 2.0749 -4.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8708 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9279 -3.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8790 -3.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2728 -1.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7728 -2.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6199 -0.2228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4250 4.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9582 -1.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 -1.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6492 -2.6601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2891 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 -0.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3546 -1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1388 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3849 0.2384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3839 -4.0270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8708 -0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 -0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2728 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0238 -2.3328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1388 -0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0019 -2.1249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2728 -0.5865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0649 2.3917 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6710 -2.8681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2728 -1.5865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3109 -1.1738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4067 -0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6418 -0.4307 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3360 -0.0706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3620 -3.8191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7369 -0.5865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4339 0.5474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7340 3.1348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7147 -3.2839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0048 -0.5865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0703 2.4962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 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 19 1 0 0 0 0 2 20 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 33 1 0 0 0 0 9 40 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 32 1 0 0 0 0 15 33 1 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 34 1 0 0 0 0 18 36 2 0 0 0 0 19 37 2 0 0 0 0 19 41 1 0 0 0 0 20 38 2 0 0 0 0 20 42 1 0 0 0 0 21 34 1 0 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 41 1 6 0 0 0 24 26 1 0 0 0 0 24 42 1 6 0 0 0 25 30 1 0 0 0 0 25 32 1 6 0 0 0 26 31 1 0 0 0 0 26 33 1 6 0 0 0 27 40 1 0 0 0 0 27 43 1 0 0 0 0 28 21 1 6 0 0 0 28 44 1 0 0 0 0 28 45 1 0 0 0 0 29 35 1 1 0 0 0 29 43 1 0 0 0 0 29 44 1 0 0 0 0 32 34 1 1 0 0 0 33 35 1 1 0 0 0 34 39 1 1 0 0 0 35 22 1 1 0 0 0 35 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	630.34
Volume:	637.297
LogP:	5.432
LogD:	3.598
LogS:	-5.052
# Rotatable Bonds:	7
TPSA:	126.82
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	6.373
Fsp3:	0.8
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:	-5.232
MDCK Permeability:	3.392467260709964e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.517
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.808

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	66.46150207519531%
Volume Distribution (VD):	2.184
Pgp-substrate:	31.667837142944336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.411
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	3.38
Half-life (T1/2):	0.003

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.348
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.99
Rat Oral Acute Toxicity:	0.999
Maximum Recommended Daily Dose:	0.128
Skin Sensitization:	0.836
Carcinogencity:	0.972
Eye Corrosion:	0.21
Eye Irritation:	0.027
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC473250

Natural Product ID:	NPC473250
*Common Name:**	Cinnafragrin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YTRTYDPOBBBIPO-UHNSDNJXSA-N
Standard InCHI:	InChI=1S/C35H50O10/c1-19(37)41-23-16-21(34(39,18-36)32(7)14-10-12-30(3,4)25(23)32)28-44-29-35(45-28)22(27(40-9)43-29)17-24(42-20(2)38)26-31(5,6)13-11-15-33(26,35)8/h16-18,23-29,39H,10-15H2,1-9H3/t23-,24-,25+,26+,27?,28+,29+,32+,33+,34-,35+/m1/s1
SMILES:	CC(=O)OC1C=C(C(C2(C1C(CCC2)(C)C)C)(C=O)O)C3OC4C5(O3)C(=CC(C6C5(CCCC6(C)C)C)OC(=O)C)C(O4)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL385716
PubChem CID:	44419504
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17286431]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT497	Individual Protein	Maltase-glucoamylase	Homo sapiens	Inhibition	=	26.5	%	PMID[513101]

☑ 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 NPC473250 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	244
0.1-0.2	1413
0.2-0.3	4398
0.3-0.4	9110
0.4-0.5	12157
0.5-0.6	7428
0.6-0.7	6022
0.7-0.8	1870
0.8-0.85	52
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9911	High Similarity	NPC473231
0.8487	Intermediate Similarity	NPC477071
0.8487	Intermediate Similarity	NPC122971
0.8475	Intermediate Similarity	NPC23046
0.8455	Intermediate Similarity	NPC470780
0.8403	Intermediate Similarity	NPC45475
0.839	Intermediate Similarity	NPC259306
0.839	Intermediate Similarity	NPC470628
0.839	Intermediate Similarity	NPC474046
0.8376	Intermediate Similarity	NPC474410
0.8376	Intermediate Similarity	NPC293658
0.8319	Intermediate Similarity	NPC258532
0.8319	Intermediate Similarity	NPC473590
0.8305	Intermediate Similarity	NPC469877
0.8305	Intermediate Similarity	NPC181145
0.8305	Intermediate Similarity	NPC470919
0.8291	Intermediate Similarity	NPC302146
0.8276	Intermediate Similarity	NPC83005
0.8246	Intermediate Similarity	NPC127609
0.8235	Intermediate Similarity	NPC474734
0.822	Intermediate Similarity	NPC75167
0.822	Intermediate Similarity	NPC311592
0.822	Intermediate Similarity	NPC157441
0.822	Intermediate Similarity	NPC56448
0.8211	Intermediate Similarity	NPC41129
0.8189	Intermediate Similarity	NPC471855
0.8182	Intermediate Similarity	NPC475775
0.8182	Intermediate Similarity	NPC474179
0.8182	Intermediate Similarity	NPC475834
0.8182	Intermediate Similarity	NPC476529
0.8167	Intermediate Similarity	NPC473968
0.816	Intermediate Similarity	NPC42399
0.8151	Intermediate Similarity	NPC472274
0.8145	Intermediate Similarity	NPC470922
0.8136	Intermediate Similarity	NPC174836
0.8136	Intermediate Similarity	NPC194951
0.8136	Intermediate Similarity	NPC12046
0.8125	Intermediate Similarity	NPC142756
0.8125	Intermediate Similarity	NPC88668
0.8125	Intermediate Similarity	NPC478151
0.812	Intermediate Similarity	NPC5103
0.8115	Intermediate Similarity	NPC107338
0.8115	Intermediate Similarity	NPC294112
0.8115	Intermediate Similarity	NPC48692
0.8115	Intermediate Similarity	NPC109607
0.811	Intermediate Similarity	NPC476074
0.811	Intermediate Similarity	NPC478065
0.811	Intermediate Similarity	NPC475377
0.811	Intermediate Similarity	NPC172374
0.811	Intermediate Similarity	NPC475167
0.811	Intermediate Similarity	NPC45346
0.811	Intermediate Similarity	NPC262796
0.811	Intermediate Similarity	NPC134914
0.811	Intermediate Similarity	NPC173435
0.811	Intermediate Similarity	NPC213634
0.811	Intermediate Similarity	NPC478064
0.811	Intermediate Similarity	NPC264566
0.811	Intermediate Similarity	NPC329993
0.811	Intermediate Similarity	NPC301639
0.8099	Intermediate Similarity	NPC475913
0.8095	Intermediate Similarity	NPC470475
0.8095	Intermediate Similarity	NPC470476
0.808	Intermediate Similarity	NPC469750
0.808	Intermediate Similarity	NPC181999
0.808	Intermediate Similarity	NPC250556
0.8077	Intermediate Similarity	NPC251998
0.8067	Intermediate Similarity	NPC469454
0.8067	Intermediate Similarity	NPC469463
0.8067	Intermediate Similarity	NPC469496
0.8065	Intermediate Similarity	NPC67251
0.8051	Intermediate Similarity	NPC304180
0.8051	Intermediate Similarity	NPC179798
0.8051	Intermediate Similarity	NPC475668
0.8051	Intermediate Similarity	NPC473921
0.8051	Intermediate Similarity	NPC475480
0.8049	Intermediate Similarity	NPC31193
0.8049	Intermediate Similarity	NPC204731
0.8049	Intermediate Similarity	NPC202051
0.8049	Intermediate Similarity	NPC242840
0.8049	Intermediate Similarity	NPC75417
0.8047	Intermediate Similarity	NPC477195
0.8047	Intermediate Similarity	NPC478152
0.8047	Intermediate Similarity	NPC478150
0.8047	Intermediate Similarity	NPC478154
0.8047	Intermediate Similarity	NPC478153
0.8034	Intermediate Similarity	NPC112457
0.8034	Intermediate Similarity	NPC472534
0.8034	Intermediate Similarity	NPC143706
0.8031	Intermediate Similarity	NPC140092
0.8031	Intermediate Similarity	NPC471407
0.8031	Intermediate Similarity	NPC188234
0.8031	Intermediate Similarity	NPC476851
0.8031	Intermediate Similarity	NPC125077
0.8031	Intermediate Similarity	NPC329986
0.8031	Intermediate Similarity	NPC232785
0.8031	Intermediate Similarity	NPC276838
0.8031	Intermediate Similarity	NPC91
0.8017	Intermediate Similarity	NPC176513
0.8017	Intermediate Similarity	NPC470775
0.8017	Intermediate Similarity	NPC293512
0.8016	Intermediate Similarity	NPC179412
0.8016	Intermediate Similarity	NPC298841
0.8016	Intermediate Similarity	NPC471356
0.8015	Intermediate Similarity	NPC596
0.8015	Intermediate Similarity	NPC295885
0.8015	Intermediate Similarity	NPC140045
0.8	Intermediate Similarity	NPC470477
0.8	Intermediate Similarity	NPC475633
0.8	Intermediate Similarity	NPC220293
0.8	Intermediate Similarity	NPC318135
0.8	Intermediate Similarity	NPC262813
0.7984	Intermediate Similarity	NPC298783
0.7984	Intermediate Similarity	NPC235438
0.7984	Intermediate Similarity	NPC107966
0.7984	Intermediate Similarity	NPC477709
0.7984	Intermediate Similarity	NPC476221
0.7984	Intermediate Similarity	NPC104585
0.7984	Intermediate Similarity	NPC225385
0.7984	Intermediate Similarity	NPC157817
0.7984	Intermediate Similarity	NPC40775
0.7984	Intermediate Similarity	NPC476779
0.7984	Intermediate Similarity	NPC249848
0.7983	Intermediate Similarity	NPC130427
0.7983	Intermediate Similarity	NPC269530
0.7983	Intermediate Similarity	NPC37739
0.7983	Intermediate Similarity	NPC46388
0.7969	Intermediate Similarity	NPC253456
0.7969	Intermediate Similarity	NPC477197
0.7969	Intermediate Similarity	NPC16569
0.7969	Intermediate Similarity	NPC478155
0.7969	Intermediate Similarity	NPC159338
0.7969	Intermediate Similarity	NPC476852
0.7969	Intermediate Similarity	NPC25998
0.7967	Intermediate Similarity	NPC471406
0.7966	Intermediate Similarity	NPC101450
0.7966	Intermediate Similarity	NPC475134
0.7966	Intermediate Similarity	NPC475563
0.7966	Intermediate Similarity	NPC235014
0.7953	Intermediate Similarity	NPC311534
0.7953	Intermediate Similarity	NPC477075
0.7953	Intermediate Similarity	NPC329923
0.7953	Intermediate Similarity	NPC475281
0.7953	Intermediate Similarity	NPC477078
0.7953	Intermediate Similarity	NPC473620
0.7951	Intermediate Similarity	NPC286347
0.7951	Intermediate Similarity	NPC18233
0.7951	Intermediate Similarity	NPC470776
0.7951	Intermediate Similarity	NPC276758
0.7939	Intermediate Similarity	NPC471089
0.7939	Intermediate Similarity	NPC141215
0.7939	Intermediate Similarity	NPC190065
0.7934	Intermediate Similarity	NPC152199
0.7934	Intermediate Similarity	NPC134869
0.7934	Intermediate Similarity	NPC235539
0.7923	Intermediate Similarity	NPC476778
0.7923	Intermediate Similarity	NPC477234
0.7923	Intermediate Similarity	NPC476777
0.792	Intermediate Similarity	NPC44716
0.792	Intermediate Similarity	NPC2370
0.792	Intermediate Similarity	NPC281148
0.792	Intermediate Similarity	NPC27363
0.792	Intermediate Similarity	NPC30735
0.792	Intermediate Similarity	NPC478066
0.792	Intermediate Similarity	NPC235405
0.7917	Intermediate Similarity	NPC138334
0.7917	Intermediate Similarity	NPC271138
0.7917	Intermediate Similarity	NPC189884
0.7917	Intermediate Similarity	NPC269315
0.7917	Intermediate Similarity	NPC204458
0.7917	Intermediate Similarity	NPC51978
0.7917	Intermediate Similarity	NPC47063
0.7917	Intermediate Similarity	NPC25909
0.7907	Intermediate Similarity	NPC42670
0.7907	Intermediate Similarity	NPC19124
0.7907	Intermediate Similarity	NPC93416
0.7899	Intermediate Similarity	NPC191763
0.7891	Intermediate Similarity	NPC477079
0.7891	Intermediate Similarity	NPC471360
0.7891	Intermediate Similarity	NPC477076
0.7891	Intermediate Similarity	NPC473593
0.7891	Intermediate Similarity	NPC180079
0.7891	Intermediate Similarity	NPC471359
0.7891	Intermediate Similarity	NPC219085
0.7891	Intermediate Similarity	NPC477196
0.7891	Intermediate Similarity	NPC17896
0.7891	Intermediate Similarity	NPC70542
0.7891	Intermediate Similarity	NPC10823
0.7891	Intermediate Similarity	NPC469754
0.7891	Intermediate Similarity	NPC469751
0.7891	Intermediate Similarity	NPC9499
0.7891	Intermediate Similarity	NPC86159
0.7891	Intermediate Similarity	NPC471358
0.7891	Intermediate Similarity	NPC470913
0.7891	Intermediate Similarity	NPC89514
0.7891	Intermediate Similarity	NPC6108
0.7891	Intermediate Similarity	NPC469755
0.7891	Intermediate Similarity	NPC471361
0.7891	Intermediate Similarity	NPC284406
0.7891	Intermediate Similarity	NPC197707
0.7891	Intermediate Similarity	NPC470912

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 NPC473250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1629
0.2-0.3	3884
0.3-0.4	2299
0.4-0.5	633
0.5-0.6	279
0.6-0.7	189
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.808	Intermediate Similarity	NPD7507	Approved
0.7891	Intermediate Similarity	NPD7319	Approved
0.7797	Intermediate Similarity	NPD6686	Approved
0.776	Intermediate Similarity	NPD8517	Approved
0.776	Intermediate Similarity	NPD8516	Approved
0.776	Intermediate Similarity	NPD8515	Approved
0.776	Intermediate Similarity	NPD8513	Phase 3
0.7724	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7736	Approved
0.7638	Intermediate Similarity	NPD8328	Phase 3
0.7603	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD8293	Discontinued
0.7583	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD6370	Approved
0.7344	Intermediate Similarity	NPD8033	Approved
0.7339	Intermediate Similarity	NPD8133	Approved
0.7308	Intermediate Similarity	NPD7492	Approved
0.7273	Intermediate Similarity	NPD6412	Phase 2
0.7266	Intermediate Similarity	NPD8294	Approved
0.7266	Intermediate Similarity	NPD6054	Approved
0.7266	Intermediate Similarity	NPD8377	Approved
0.7266	Intermediate Similarity	NPD6059	Approved
0.7252	Intermediate Similarity	NPD6616	Approved
0.7244	Intermediate Similarity	NPD7328	Approved
0.7244	Intermediate Similarity	NPD7327	Approved
0.7209	Intermediate Similarity	NPD8380	Approved
0.7209	Intermediate Similarity	NPD8379	Approved
0.7209	Intermediate Similarity	NPD8296	Approved
0.7209	Intermediate Similarity	NPD8378	Approved
0.7209	Intermediate Similarity	NPD8335	Approved
0.7197	Intermediate Similarity	NPD7078	Approved
0.7188	Intermediate Similarity	NPD7516	Approved
0.712	Intermediate Similarity	NPD8297	Approved
0.712	Intermediate Similarity	NPD6882	Approved
0.7097	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6016	Approved
0.7077	Intermediate Similarity	NPD6015	Approved
0.7077	Intermediate Similarity	NPD7503	Approved
0.7073	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD8074	Phase 3
0.7031	Intermediate Similarity	NPD6009	Approved
0.7031	Intermediate Similarity	NPD7115	Discovery
0.7023	Intermediate Similarity	NPD5988	Approved
0.7016	Intermediate Similarity	NPD6373	Approved
0.7016	Intermediate Similarity	NPD6372	Approved
0.6992	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7320	Approved
0.6917	Remote Similarity	NPD7640	Approved
0.6917	Remote Similarity	NPD7639	Approved
0.6911	Remote Similarity	NPD6675	Approved
0.6911	Remote Similarity	NPD7128	Approved
0.6911	Remote Similarity	NPD6008	Approved
0.6911	Remote Similarity	NPD5739	Approved
0.6911	Remote Similarity	NPD6402	Approved
0.6905	Remote Similarity	NPD6650	Approved
0.6905	Remote Similarity	NPD6649	Approved
0.688	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6319	Approved
0.6861	Remote Similarity	NPD7260	Phase 2
0.6855	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6053	Discontinued
0.6838	Remote Similarity	NPD6399	Phase 3
0.6833	Remote Similarity	NPD4225	Approved
0.6833	Remote Similarity	NPD7638	Approved
0.6812	Remote Similarity	NPD6845	Suspended
0.68	Remote Similarity	NPD6881	Approved
0.68	Remote Similarity	NPD6899	Approved
0.6797	Remote Similarity	NPD4632	Approved
0.6772	Remote Similarity	NPD8130	Phase 1
0.6765	Remote Similarity	NPD6033	Approved
0.675	Remote Similarity	NPD7902	Approved
0.672	Remote Similarity	NPD5697	Approved
0.672	Remote Similarity	NPD5701	Approved
0.6695	Remote Similarity	NPD5779	Approved
0.6695	Remote Similarity	NPD5778	Approved
0.6694	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6883	Approved
0.6693	Remote Similarity	NPD7290	Approved
0.6693	Remote Similarity	NPD7102	Approved
0.6641	Remote Similarity	NPD6617	Approved
0.6641	Remote Similarity	NPD6847	Approved
0.6641	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD7748	Approved
0.6618	Remote Similarity	NPD8451	Approved
0.6614	Remote Similarity	NPD6014	Approved
0.6614	Remote Similarity	NPD6013	Approved
0.6614	Remote Similarity	NPD6012	Approved
0.6612	Remote Similarity	NPD6083	Phase 2
0.6612	Remote Similarity	NPD6084	Phase 2
0.661	Remote Similarity	NPD7983	Approved
0.6593	Remote Similarity	NPD6067	Discontinued
0.6593	Remote Similarity	NPD7604	Phase 2
0.6583	Remote Similarity	NPD5695	Phase 3
0.6569	Remote Similarity	NPD8448	Approved
0.6567	Remote Similarity	NPD6921	Approved
0.6567	Remote Similarity	NPD5983	Phase 2
0.6557	Remote Similarity	NPD5696	Approved
0.6547	Remote Similarity	NPD8392	Approved
0.6547	Remote Similarity	NPD8390	Approved
0.6547	Remote Similarity	NPD8391	Approved
0.6544	Remote Similarity	NPD8340	Approved
0.6544	Remote Similarity	NPD8342	Approved
0.6544	Remote Similarity	NPD8299	Approved
0.6544	Remote Similarity	NPD8341	Approved
0.6535	Remote Similarity	NPD6011	Approved
0.6532	Remote Similarity	NPD5211	Phase 2
0.6529	Remote Similarity	NPD4697	Phase 3
0.6525	Remote Similarity	NPD46	Approved
0.6525	Remote Similarity	NPD6698	Approved
0.6512	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7900	Approved
0.65	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6336	Discontinued
0.6475	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD6411	Approved
0.6471	Remote Similarity	NPD8035	Phase 2
0.6442	Remote Similarity	NPD7799	Discontinued
0.6434	Remote Similarity	NPD6371	Approved
0.6429	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7632	Discontinued
0.6389	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5285	Approved
0.6371	Remote Similarity	NPD5286	Approved
0.6371	Remote Similarity	NPD4700	Approved
0.6371	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD5282	Discontinued
0.6356	Remote Similarity	NPD6672	Approved
0.6356	Remote Similarity	NPD5737	Approved
0.6333	Remote Similarity	NPD5693	Phase 1
0.6333	Remote Similarity	NPD7515	Phase 2
0.6324	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6274	Approved
0.6312	Remote Similarity	NPD5956	Approved
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD4634	Approved
0.6303	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6101	Approved
0.6296	Remote Similarity	NPD7101	Approved
0.6296	Remote Similarity	NPD7100	Approved
0.6293	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5225	Approved
0.627	Remote Similarity	NPD5224	Approved
0.627	Remote Similarity	NPD4633	Approved
0.627	Remote Similarity	NPD5226	Approved
0.6261	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD1694	Approved
0.6232	Remote Similarity	NPD7122	Discontinued
0.6232	Remote Similarity	NPD7642	Approved
0.6222	Remote Similarity	NPD6335	Approved
0.622	Remote Similarity	NPD5174	Approved
0.622	Remote Similarity	NPD5175	Approved
0.6218	Remote Similarity	NPD6903	Approved
0.6218	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6908	Approved
0.6204	Remote Similarity	NPD6909	Approved
0.6198	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD5344	Discontinued
0.6186	Remote Similarity	NPD7146	Approved
0.6186	Remote Similarity	NPD7521	Approved
0.6186	Remote Similarity	NPD6409	Approved
0.6186	Remote Similarity	NPD5330	Approved
0.6186	Remote Similarity	NPD6098	Approved
0.6186	Remote Similarity	NPD6684	Approved
0.6186	Remote Similarity	NPD7334	Approved
0.6167	Remote Similarity	NPD6080	Approved
0.6167	Remote Similarity	NPD4753	Phase 2
0.6167	Remote Similarity	NPD6673	Approved
0.6167	Remote Similarity	NPD5328	Approved
0.6167	Remote Similarity	NPD6051	Approved
0.6167	Remote Similarity	NPD6904	Approved
0.6154	Remote Similarity	NPD4786	Approved
0.6154	Remote Similarity	NPD4729	Approved
0.6154	Remote Similarity	NPD4730	Approved
0.6148	Remote Similarity	NPD6317	Approved
0.6134	Remote Similarity	NPD3573	Approved
0.6129	Remote Similarity	NPD5221	Approved
0.6129	Remote Similarity	NPD5222	Approved
0.6129	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD3667	Approved
0.6116	Remote Similarity	NPD7838	Discovery
0.6115	Remote Similarity	NPD7830	Approved
0.6115	Remote Similarity	NPD7829	Approved
0.6111	Remote Similarity	NPD6648	Approved
0.6103	Remote Similarity	NPD6314	Approved
0.6103	Remote Similarity	NPD7641	Discontinued
0.6103	Remote Similarity	NPD6313	Approved
0.6094	Remote Similarity	NPD4754	Approved
0.6087	Remote Similarity	NPD8268	Approved
0.6087	Remote Similarity	NPD8266	Approved
0.6087	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8444	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