NPASS Compound

Structure

NPC475223 OpenBabel07101718192D 46 52 0 0 1 0 0 0 0 0999 V2000 3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3268 2.1861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1189 3.1642 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 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 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 2.5981 3.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3218 2.1168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3272 2.2213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7285 3.0303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 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 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7067 3.2382 0.0000 C 0 0 1 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 -1.1193 3.1994 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3758 2.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 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 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0157 4.1893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2058 3.6062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0668 1.5440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9854 3.6994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 33 1 0 0 0 0 2 33 1 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 6 36 1 0 0 0 0 7 39 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 21 2 0 0 0 0 11 24 2 0 0 0 0 12 17 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 29 1 0 0 0 0 15 35 1 0 0 0 0 16 37 1 0 0 0 0 18 25 1 0 0 0 0 19 27 1 0 0 0 0 19 28 1 0 0 0 0 20 37 1 0 0 0 0 20 38 1 0 0 0 0 21 24 1 0 0 0 0 21 31 1 0 0 0 0 22 18 1 6 0 0 0 22 23 1 0 0 0 0 22 32 1 0 0 0 0 23 37 1 6 0 0 0 24 39 1 0 0 0 0 25 30 1 6 0 0 0 25 45 1 0 0 0 0 26 35 1 6 0 0 0 26 36 1 0 0 0 0 27 33 1 0 0 0 0 27 35 1 6 0 0 0 28 36 1 1 0 0 0 28 40 1 0 0 0 0 29 33 1 0 0 0 0 29 46 1 6 0 0 0 30 34 1 0 0 0 0 30 41 1 1 0 0 0 31 42 2 0 0 0 0 31 46 1 0 0 0 0 32 43 1 0 0 0 0 32 45 1 0 0 0 0 34 44 1 0 0 0 0 35 5 1 6 0 0 0 36 38 1 1 0 0 0 37 38 1 1 0 0 0 38 17 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	639.41
Volume:	667.891
LogP:	4.69
LogD:	3.989
LogS:	-4.581
# Rotatable Bonds:	7
TPSA:	128.48
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	5.505
Fsp3:	0.816
Lipinski Rule-of-5:	Accepted
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:	-5.206
MDCK Permeability:	1.3445553122437559e-05
Pgp-inhibitor:	0.221
Pgp-substrate:	0.367
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.797

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	93.03194427490234%
Volume Distribution (VD):	1.792
Pgp-substrate:	6.415294647216797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.213
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.213
CYP3A4-inhibitor:	0.655
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	5.926
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.536
Human Hepatotoxicity (H-HT):	0.3
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.83
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.808
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC475223

Natural Product ID:	NPC475223
*Common Name:**	FJSCIFMDQSXLCX-CVKWUQFVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FJSCIFMDQSXLCX-CVKWUQFVSA-N
Standard InCHI:	InChI=1S/C38H57NO7/c1-33(2)27-19-28(40)36(6)26(35(27,5)15-14-29(33)46-31(42)21-10-8-9-11-24(21)39-7)13-16-37-20-38(36,37)17-12-23(37)22-18-25(45-32(22)43)30(41)34(3,4)44/h8-11,22-23,25-30,32,39-41,43-44H,12-20H2,1-7H3/t22-,23-,25+,26+,27-,28+,29-,30-,32?,35+,36-,37+,38+/m0/s1
SMILES:	CNc1ccccc1C(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)C[C@H]([C@@]1([C@@H]2CC[C@@]23[C@]1(CC[C@H]3[C@@H]1C[C@@H](OC1O)[C@@H](C(O)(C)C)O)C2)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501381
PubChem CID:	21668677
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO8325	Raulinoa echinata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11704964]
NPO8325	Raulinoa echinata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975501]
NPO8325	Raulinoa echinata	Species	Rutaceae	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
IC50	1
LD50	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	1000.0	ug.mL-1	PMID[484561]
NPT176	Organism	Artemia salina	Artemia salina	LD50	>	100.0	ug ml-1	PMID[484561]

☑ 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 NPC475223 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	277
0.1-0.2	1298
0.2-0.3	2711
0.3-0.4	7355
0.4-0.5	19561
0.5-0.6	9560
0.6-0.7	1761
0.7-0.8	162
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9944	High Similarity	NPC475448
0.9944	High Similarity	NPC246983
0.877	High Similarity	NPC21483
0.877	High Similarity	NPC198205
0.873	High Similarity	NPC112752
0.873	High Similarity	NPC311054
0.8684	High Similarity	NPC107828
0.8684	High Similarity	NPC90358
0.8677	High Similarity	NPC198390
0.8594	High Similarity	NPC176371
0.8594	High Similarity	NPC136573
0.7933	Intermediate Similarity	NPC223590
0.7923	Intermediate Similarity	NPC473837
0.779	Intermediate Similarity	NPC472657
0.779	Intermediate Similarity	NPC472658
0.7778	Intermediate Similarity	NPC475316
0.7778	Intermediate Similarity	NPC473486
0.7731	Intermediate Similarity	NPC470631
0.7731	Intermediate Similarity	NPC473781
0.7731	Intermediate Similarity	NPC35390
0.77	Intermediate Similarity	NPC473667
0.7642	Intermediate Similarity	NPC140311
0.7606	Intermediate Similarity	NPC470971
0.76	Intermediate Similarity	NPC476218
0.76	Intermediate Similarity	NPC108804
0.757	Intermediate Similarity	NPC106593
0.755	Intermediate Similarity	NPC476256
0.755	Intermediate Similarity	NPC476206
0.755	Intermediate Similarity	NPC476205
0.755	Intermediate Similarity	NPC476129
0.755	Intermediate Similarity	NPC476212
0.755	Intermediate Similarity	NPC476257
0.755	Intermediate Similarity	NPC476207
0.755	Intermediate Similarity	NPC259791
0.7387	Intermediate Similarity	NPC316405
0.73	Intermediate Similarity	NPC477998
0.7294	Intermediate Similarity	NPC471980
0.7269	Intermediate Similarity	NPC301368
0.7269	Intermediate Similarity	NPC84815
0.7248	Intermediate Similarity	NPC127720
0.7248	Intermediate Similarity	NPC127026
0.7243	Intermediate Similarity	NPC475561
0.7243	Intermediate Similarity	NPC475417
0.724	Intermediate Similarity	NPC475644
0.724	Intermediate Similarity	NPC471190
0.724	Intermediate Similarity	NPC470486
0.724	Intermediate Similarity	NPC471977
0.7225	Intermediate Similarity	NPC253738
0.7222	Intermediate Similarity	NPC294579
0.7222	Intermediate Similarity	NPC144779
0.722	Intermediate Similarity	NPC30456
0.7202	Intermediate Similarity	NPC30171
0.7195	Intermediate Similarity	NPC475600
0.7195	Intermediate Similarity	NPC122968
0.7195	Intermediate Similarity	NPC476110
0.7195	Intermediate Similarity	NPC477787
0.7195	Intermediate Similarity	NPC228377
0.7195	Intermediate Similarity	NPC475631
0.7195	Intermediate Similarity	NPC328186
0.7195	Intermediate Similarity	NPC87152
0.7182	Intermediate Similarity	NPC475137
0.7182	Intermediate Similarity	NPC475498
0.7182	Intermediate Similarity	NPC473850
0.7176	Intermediate Similarity	NPC471016
0.7176	Intermediate Similarity	NPC471014
0.7176	Intermediate Similarity	NPC475408
0.7176	Intermediate Similarity	NPC6981
0.7175	Intermediate Similarity	NPC475596
0.7175	Intermediate Similarity	NPC316841
0.7175	Intermediate Similarity	NPC475303
0.7174	Intermediate Similarity	NPC473602
0.7158	Intermediate Similarity	NPC475122
0.7158	Intermediate Similarity	NPC476784
0.7157	Intermediate Similarity	NPC205
0.7157	Intermediate Similarity	NPC124690
0.7157	Intermediate Similarity	NPC172769
0.7157	Intermediate Similarity	NPC184195
0.7157	Intermediate Similarity	NPC281470
0.7157	Intermediate Similarity	NPC166521
0.7151	Intermediate Similarity	NPC469448
0.7149	Intermediate Similarity	NPC473506
0.7143	Intermediate Similarity	NPC62367
0.7136	Intermediate Similarity	NPC76565
0.7136	Intermediate Similarity	NPC57797
0.7136	Intermediate Similarity	NPC250807
0.713	Intermediate Similarity	NPC470306
0.713	Intermediate Similarity	NPC477907
0.713	Intermediate Similarity	NPC477909
0.713	Intermediate Similarity	NPC42678
0.7128	Intermediate Similarity	NPC114808
0.712	Intermediate Similarity	NPC96903
0.712	Intermediate Similarity	NPC174982
0.712	Intermediate Similarity	NPC29704
0.712	Intermediate Similarity	NPC472572
0.712	Intermediate Similarity	NPC184817
0.712	Intermediate Similarity	NPC472571
0.712	Intermediate Similarity	NPC472575
0.712	Intermediate Similarity	NPC472568
0.712	Intermediate Similarity	NPC158663
0.712	Intermediate Similarity	NPC171525
0.712	Intermediate Similarity	NPC470159
0.712	Intermediate Similarity	NPC70403
0.712	Intermediate Similarity	NPC473088
0.712	Intermediate Similarity	NPC470157
0.712	Intermediate Similarity	NPC469349
0.712	Intermediate Similarity	NPC200471
0.712	Intermediate Similarity	NPC177940
0.712	Intermediate Similarity	NPC471104
0.712	Intermediate Similarity	NPC476973
0.7117	Intermediate Similarity	NPC211920
0.7113	Intermediate Similarity	NPC477491
0.7111	Intermediate Similarity	NPC237702
0.711	Intermediate Similarity	NPC216428
0.7104	Intermediate Similarity	NPC477902
0.7104	Intermediate Similarity	NPC328154
0.7104	Intermediate Similarity	NPC91703
0.7098	Intermediate Similarity	NPC292416
0.7098	Intermediate Similarity	NPC473689
0.7094	Intermediate Similarity	NPC471623
0.709	Intermediate Similarity	NPC34066
0.7085	Intermediate Similarity	NPC475362
0.7083	Intermediate Similarity	NPC4421
0.708	Intermediate Similarity	NPC475406
0.7067	Intermediate Similarity	NPC244839
0.7067	Intermediate Similarity	NPC320324
0.7067	Intermediate Similarity	NPC319880
0.7065	Intermediate Similarity	NPC475759
0.7065	Intermediate Similarity	NPC472573
0.7065	Intermediate Similarity	NPC476974
0.7065	Intermediate Similarity	NPC11685
0.7065	Intermediate Similarity	NPC472570
0.7065	Intermediate Similarity	NPC470152
0.7065	Intermediate Similarity	NPC188865
0.7065	Intermediate Similarity	NPC70716
0.7065	Intermediate Similarity	NPC472569
0.7065	Intermediate Similarity	NPC25768
0.7065	Intermediate Similarity	NPC163719
0.7065	Intermediate Similarity	NPC95265
0.7065	Intermediate Similarity	NPC241951
0.7065	Intermediate Similarity	NPC125106
0.7065	Intermediate Similarity	NPC57628
0.7065	Intermediate Similarity	NPC95810
0.7064	Intermediate Similarity	NPC473089
0.7064	Intermediate Similarity	NPC212768
0.7064	Intermediate Similarity	NPC6576
0.7064	Intermediate Similarity	NPC158020
0.7064	Intermediate Similarity	NPC473115
0.7064	Intermediate Similarity	NPC75600
0.7048	Intermediate Similarity	NPC327904
0.7048	Intermediate Similarity	NPC38959
0.7045	Intermediate Similarity	NPC477912
0.7044	Intermediate Similarity	NPC327699
0.7042	Intermediate Similarity	NPC470280
0.704	Intermediate Similarity	NPC146824
0.704	Intermediate Similarity	NPC124029
0.7039	Intermediate Similarity	NPC173295
0.7039	Intermediate Similarity	NPC48929
0.7033	Intermediate Similarity	NPC100913
0.7033	Intermediate Similarity	NPC275592
0.7031	Intermediate Similarity	NPC471138
0.7031	Intermediate Similarity	NPC326328
0.7031	Intermediate Similarity	NPC309991
0.7031	Intermediate Similarity	NPC323356
0.7027	Intermediate Similarity	NPC472556
0.7026	Intermediate Similarity	NPC473557
0.7026	Intermediate Similarity	NPC473468
0.7026	Intermediate Similarity	NPC475567
0.7024	Intermediate Similarity	NPC108276
0.7024	Intermediate Similarity	NPC163578
0.7022	Intermediate Similarity	NPC96801
0.7022	Intermediate Similarity	NPC150698
0.7016	Intermediate Similarity	NPC318447
0.7016	Intermediate Similarity	NPC322048
0.7015	Intermediate Similarity	NPC97584
0.7014	Intermediate Similarity	NPC477788
0.7011	Intermediate Similarity	NPC163087
0.7005	Intermediate Similarity	NPC471101
0.7005	Intermediate Similarity	NPC477488
0.7005	Intermediate Similarity	NPC92293
0.7005	Intermediate Similarity	NPC266265
0.7005	Intermediate Similarity	NPC301556
0.7005	Intermediate Similarity	NPC473215
0.7005	Intermediate Similarity	NPC270590
0.7005	Intermediate Similarity	NPC476975
0.7004	Intermediate Similarity	NPC170751
0.7004	Intermediate Similarity	NPC327769
0.7	Intermediate Similarity	NPC469422
0.6996	Remote Similarity	NPC148860
0.6995	Remote Similarity	NPC472576
0.6995	Remote Similarity	NPC118080
0.6995	Remote Similarity	NPC87448
0.6995	Remote Similarity	NPC291599
0.6995	Remote Similarity	NPC16912
0.6995	Remote Similarity	NPC41481
0.6995	Remote Similarity	NPC97947
0.6995	Remote Similarity	NPC27377
0.6991	Remote Similarity	NPC472553
0.699	Remote Similarity	NPC475175
0.699	Remote Similarity	NPC475531
0.699	Remote Similarity	NPC475198

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 NPC475223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	577
0.2-0.3	752
0.3-0.4	1964
0.4-0.5	3920
0.5-0.6	1643
0.6-0.7	111
0.7-0.8	1
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
0.7337	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2836	Approved
0.7136	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8435	Approved
0.7094	Intermediate Similarity	NPD8361	Approved
0.7094	Intermediate Similarity	NPD8360	Approved
0.705	Intermediate Similarity	NPD7962	Phase 2
0.697	Remote Similarity	NPD7799	Discontinued
0.6952	Remote Similarity	NPD4888	Discontinued
0.6927	Remote Similarity	NPD5928	Phase 1
0.688	Remote Similarity	NPD8468	Phase 2
0.6872	Remote Similarity	NPD5430	Discontinued
0.6872	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8407	Phase 2
0.681	Remote Similarity	NPD8485	Approved
0.6806	Remote Similarity	NPD5086	Approved
0.6791	Remote Similarity	NPD7295	Approved
0.6789	Remote Similarity	NPD7606	Phase 3
0.6774	Remote Similarity	NPD1625	Approved
0.6772	Remote Similarity	NPD7528	Approved
0.6762	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7487	Discontinued
0.6736	Remote Similarity	NPD2672	Discontinued
0.6713	Remote Similarity	NPD7999	Approved
0.67	Remote Similarity	NPD5997	Discontinued
0.6699	Remote Similarity	NPD8146	Phase 2
0.6698	Remote Similarity	NPD4668	Phase 2
0.6698	Remote Similarity	NPD7497	Discontinued
0.6698	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5466	Approved
0.6667	Remote Similarity	NPD8368	Discontinued
0.6667	Remote Similarity	NPD6723	Discontinued
0.6649	Remote Similarity	NPD1626	Approved
0.6632	Remote Similarity	NPD7478	Approved
0.6631	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7930	Approved
0.6617	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8462	Phase 1
0.6589	Remote Similarity	NPD6874	Approved
0.6579	Remote Similarity	NPD7236	Approved
0.654	Remote Similarity	NPD7569	Approved
0.654	Remote Similarity	NPD7570	Approved
0.6526	Remote Similarity	NPD5411	Discontinued
0.6522	Remote Similarity	NPD7546	Discontinued
0.652	Remote Similarity	NPD5498	Phase 2
0.6508	Remote Similarity	NPD7082	Approved
0.6502	Remote Similarity	NPD3795	Approved
0.6502	Remote Similarity	NPD3794	Approved
0.6495	Remote Similarity	NPD7239	Suspended
0.6476	Remote Similarity	NPD7693	Approved
0.6474	Remote Similarity	NPD7259	Approved
0.6465	Remote Similarity	NPD7700	Phase 2
0.6465	Remote Similarity	NPD7699	Phase 2
0.6456	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1189	Approved
0.6438	Remote Similarity	NPD8319	Approved
0.6438	Remote Similarity	NPD8320	Phase 1
0.6425	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD2670	Approved
0.6411	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6534	Approved
0.6402	Remote Similarity	NPD6535	Approved
0.6402	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7256	Discontinued
0.6389	Remote Similarity	NPD5197	Approved
0.6389	Remote Similarity	NPD5196	Approved
0.6389	Remote Similarity	NPD5194	Approved
0.6385	Remote Similarity	NPD5937	Approved
0.638	Remote Similarity	NPD7583	Approved
0.6378	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD7476	Discontinued
0.6373	Remote Similarity	NPD1801	Approved
0.6373	Remote Similarity	NPD1802	Approved
0.6364	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7795	Phase 2
0.6351	Remote Similarity	NPD4859	Phase 1
0.6351	Remote Similarity	NPD7585	Approved
0.6351	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD8404	Phase 2
0.6337	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8167	Discontinued
0.6323	Remote Similarity	NPD4506	Discontinued
0.6318	Remote Similarity	NPD7435	Discontinued
0.6316	Remote Similarity	NPD8281	Discontinued
0.6314	Remote Similarity	NPD7922	Phase 1
0.6313	Remote Similarity	NPD6677	Suspended
0.6311	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD2821	Approved
0.6296	Remote Similarity	NPD3170	Approved
0.6291	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD7300	Phase 3
0.6278	Remote Similarity	NPD7302	Phase 3
0.6277	Remote Similarity	NPD6995	Phase 1
0.6276	Remote Similarity	NPD1230	Approved
0.6273	Remote Similarity	NPD6823	Phase 2
0.627	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7801	Approved
0.6262	Remote Similarity	NPD5042	Phase 1
0.6256	Remote Similarity	NPD6779	Approved
0.6256	Remote Similarity	NPD6777	Approved
0.6256	Remote Similarity	NPD6781	Approved
0.6256	Remote Similarity	NPD6778	Approved
0.6256	Remote Similarity	NPD6776	Approved
0.6256	Remote Similarity	NPD6782	Approved
0.6256	Remote Similarity	NPD6780	Approved
0.625	Remote Similarity	NPD7479	Phase 2
0.625	Remote Similarity	NPD2820	Phase 3
0.6245	Remote Similarity	NPD6625	Approved
0.6245	Remote Similarity	NPD7878	Phase 2
0.6244	Remote Similarity	NPD7698	Approved
0.6244	Remote Similarity	NPD7696	Phase 3
0.6244	Remote Similarity	NPD7697	Approved
0.6238	Remote Similarity	NPD8007	Approved
0.6238	Remote Similarity	NPD8008	Approved
0.6233	Remote Similarity	NPD7584	Approved
0.6229	Remote Similarity	NPD7688	Phase 1
0.6225	Remote Similarity	NPD8127	Discontinued
0.6225	Remote Similarity	NPD6457	Approved
0.6221	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD7244	Discontinued
0.6216	Remote Similarity	NPD7891	Discontinued
0.6216	Remote Similarity	NPD7871	Phase 2
0.6216	Remote Similarity	NPD7870	Phase 2
0.6215	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5609	Approved
0.621	Remote Similarity	NPD5608	Approved
0.621	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD2509	Approved
0.6205	Remote Similarity	NPD2510	Approved
0.6204	Remote Similarity	NPD6212	Phase 3
0.6204	Remote Similarity	NPD6213	Phase 3
0.6204	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD2365	Approved
0.6197	Remote Similarity	NPD6891	Phase 2
0.6197	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7783	Phase 2
0.6192	Remote Similarity	NPD7853	Phase 2
0.619	Remote Similarity	NPD3280	Approved
0.619	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7039	Approved
0.619	Remote Similarity	NPD7038	Approved
0.6172	Remote Similarity	NPD7881	Approved
0.617	Remote Similarity	NPD8059	Phase 3
0.617	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7827	Phase 1
0.6167	Remote Similarity	NPD7301	Phase 3
0.6161	Remote Similarity	NPD6296	Discontinued
0.6157	Remote Similarity	NPD3394	Approved
0.6157	Remote Similarity	NPD3389	Approved
0.6157	Remote Similarity	NPD3393	Approved
0.6154	Remote Similarity	NPD6620	Discovery
0.6154	Remote Similarity	NPD4607	Approved
0.615	Remote Similarity	NPD7105	Phase 1
0.6147	Remote Similarity	NPD5582	Discontinued
0.6143	Remote Similarity	NPD1294	Discontinued
0.6143	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD4513	Discontinued
0.6137	Remote Similarity	NPD6997	Phase 2
0.6135	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7854	Phase 2
0.6134	Remote Similarity	NPD2387	Approved
0.6133	Remote Similarity	NPD4082	Approved
0.6133	Remote Similarity	NPD7701	Phase 2
0.613	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5610	Approved
0.6128	Remote Similarity	NPD7186	Phase 3
0.6127	Remote Similarity	NPD7036	Phase 3
0.6127	Remote Similarity	NPD7035	Approved
0.6127	Remote Similarity	NPD6315	Phase 2
0.6126	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6123	Remote Similarity	NPD1945	Phase 1
0.6123	Remote Similarity	NPD4493	Discontinued
0.6122	Remote Similarity	NPD6758	Approved
0.6121	Remote Similarity	NPD6484	Approved
0.6121	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6483	Approved
0.6121	Remote Similarity	NPD3437	Discontinued
0.6118	Remote Similarity	NPD4981	Phase 2
0.6117	Remote Similarity	NPD5186	Approved
0.6117	Remote Similarity	NPD5183	Approved
0.6116	Remote Similarity	NPD7010	Phase 3
0.6114	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7708	Approved
0.6111	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD7057	Phase 3
0.6108	Remote Similarity	NPD7058	Phase 2
0.6099	Remote Similarity	NPD6176	Phase 1
0.6095	Remote Similarity	NPD7775	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