NPASS Compound

Structure

NPC475330 OpenBabel07101718302D 53 58 0 0 1 0 0 0 0 0999 V2000 1.0945 -3.6911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1421 -2.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4426 2.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3240 3.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3396 2.6634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5710 1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9652 3.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3907 -0.6097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3907 -1.3640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7374 -0.2326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7374 -1.7411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0842 -0.6097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4310 -1.7411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5036 -2.7779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6205 0.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0098 -0.4978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7853 -2.7988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6571 2.5432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2135 1.8304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4188 2.7461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0842 -1.3640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9750 -1.1403 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5891 -2.2603 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1611 0.6584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4459 -0.7382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5937 -2.3107 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0175 2.0821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7062 1.1469 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1840 2.2952 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2724 -1.9045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7773 1.3949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9021 -1.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3938 1.8834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6071 -2.6297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1998 2.3395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2174 -0.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4262 0.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2211 -1.1650 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0362 -1.7825 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6220 0.1088 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1449 -0.1967 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7624 -1.3816 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0045 1.2937 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5458 1.0771 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7307 1.6946 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9348 -2.2757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1484 2.0572 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5970 -2.3088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6986 2.1885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0126 -2.9626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9267 2.7683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6486 -0.0885 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 19 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 12 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 21 1 0 0 0 0 14 50 1 0 0 0 0 15 24 2 0 0 0 0 15 52 1 0 0 0 0 16 25 2 0 0 0 0 16 53 1 0 0 0 0 20 7 1 1 0 0 0 20 29 1 0 0 0 0 20 51 1 0 0 0 0 22 13 1 1 0 0 0 22 36 1 0 0 0 0 22 38 1 0 0 0 0 23 14 1 6 0 0 0 23 30 1 0 0 0 0 23 39 1 0 0 0 0 24 31 1 0 0 0 0 24 40 1 0 0 0 0 25 32 1 0 0 0 0 25 41 1 0 0 0 0 26 17 1 6 0 0 0 26 34 1 0 0 0 0 26 42 1 0 0 0 0 27 18 1 6 0 0 0 27 35 1 0 0 0 0 27 43 1 0 0 0 0 28 19 1 1 0 0 0 28 37 1 0 0 0 0 28 44 1 0 0 0 0 29 33 1 6 0 0 0 29 45 1 0 0 0 0 30 38 2 3 0 0 0 30 46 1 0 0 0 0 31 43 2 3 0 0 0 31 47 1 0 0 0 0 32 42 2 3 0 0 0 32 48 1 0 0 0 0 33 44 2 3 0 0 0 33 49 1 0 0 0 0 34 39 2 0 0 0 0 34 50 1 0 0 0 0 35 45 2 0 0 0 0 35 51 1 0 0 0 0 36 40 2 0 0 0 0 36 52 1 0 0 0 0 37 41 2 0 0 0 0 37 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	762.3
Volume:	740.629
LogP:	4.3
LogD:	3.609
LogS:	-2.296
# Rotatable Bonds:	5
TPSA:	203.43
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	7.661
Fsp3:	0.486
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:	-4.774
MDCK Permeability:	1.9970735593233258e-05
Pgp-inhibitor:	0.806
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.499
Plasma Protein Binding (PPB):	65.5446548461914%
Volume Distribution (VD):	1.492
Pgp-substrate:	16.250076293945312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	1.316
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.994
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.473
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.004
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.206

Download Data

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

Natural Product: NPC475330

Natural Product ID:	NPC475330
*Common Name:**	Patellamide F
IUPAC Name:	n.a.
Synonyms:	Patellamide F
Standard InCHIKey:	DIJMIACMPAVWLR-HJXMHUEUSA-N
Standard InCHI:	InChI=1S/C37H46N8O6S2/c1-17(2)26-34-39-23(14-50-34)30(46)38-22(13-21-11-9-8-10-12-21)36-40-24(15-52-36)31(47)43-27(18(3)4)35-45-29(20(7)51-35)33(49)44-28(19(5)6)37-41-25(16-53-37)32(48)42-26/h8-12,15-20,22-23,26-29H,13-14H2,1-7H3,(H,38,46)(H,42,48)(H,43,47)(H,44,49)/t20-,22-,23+,26+,27+,28-,29+/m1/s1
SMILES:	OC1=N[C@H](Cc2ccccc2)c2scc(n2)C(=N[C@@H](C(C)C)C2=N[C@@H]([C@H](O2)C)C(=N[C@@H](c2nc(C(=N[C@H](C3=N[C@H]1CO3)C(C)C)O)cs2)C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503588
PubChem CID:	392480
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0001995] Cyclic peptides

*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
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593285]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2095371]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809606]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623037]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868162]
NPO4712	Lissoclinum patella	Species	Didemnidae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	48000.0	nM	PMID[465799]

☑ 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 NPC475330 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	235
0.1-0.2	2515
0.2-0.3	15794
0.3-0.4	17714
0.4-0.5	5138
0.5-0.6	1223
0.6-0.7	47
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC174652
0.9938	High Similarity	NPC229160
0.9938	High Similarity	NPC263485
0.9938	High Similarity	NPC25316
0.9689	High Similarity	NPC476080
0.9689	High Similarity	NPC161242
0.9689	High Similarity	NPC475534
0.9259	High Similarity	NPC476103
0.9198	High Similarity	NPC24990
0.7967	Intermediate Similarity	NPC329961
0.7944	Intermediate Similarity	NPC96016
0.788	Intermediate Similarity	NPC165538
0.7869	Intermediate Similarity	NPC122427
0.7688	Intermediate Similarity	NPC120917
0.765	Intermediate Similarity	NPC49051
0.7625	Intermediate Similarity	NPC74917
0.7375	Intermediate Similarity	NPC89592
0.7286	Intermediate Similarity	NPC145178
0.7286	Intermediate Similarity	NPC475350
0.7286	Intermediate Similarity	NPC14877
0.7264	Intermediate Similarity	NPC251036
0.7233	Intermediate Similarity	NPC51692
0.7166	Intermediate Similarity	NPC161143
0.715	Intermediate Similarity	NPC106235
0.715	Intermediate Similarity	NPC239660
0.7125	Intermediate Similarity	NPC267605
0.7044	Intermediate Similarity	NPC135558
0.6897	Remote Similarity	NPC319751
0.6884	Remote Similarity	NPC469858
0.6818	Remote Similarity	NPC473398
0.6813	Remote Similarity	NPC214375
0.678	Remote Similarity	NPC119481
0.6724	Remote Similarity	NPC469801
0.6697	Remote Similarity	NPC475196
0.6618	Remote Similarity	NPC75498
0.6554	Remote Similarity	NPC475390
0.6536	Remote Similarity	NPC283783
0.65	Remote Similarity	NPC313966
0.65	Remote Similarity	NPC314254
0.6489	Remote Similarity	NPC475920
0.6443	Remote Similarity	NPC249662
0.6402	Remote Similarity	NPC79386
0.6368	Remote Similarity	NPC470146
0.6368	Remote Similarity	NPC101980
0.6368	Remote Similarity	NPC97078
0.6364	Remote Similarity	NPC478030
0.6321	Remote Similarity	NPC317725
0.6321	Remote Similarity	NPC317362
0.6321	Remote Similarity	NPC318930
0.6321	Remote Similarity	NPC326407
0.6307	Remote Similarity	NPC89489
0.6268	Remote Similarity	NPC257511
0.6257	Remote Similarity	NPC315252
0.6234	Remote Similarity	NPC75609
0.6234	Remote Similarity	NPC140284
0.6223	Remote Similarity	NPC237219
0.6176	Remote Similarity	NPC475568
0.6166	Remote Similarity	NPC164006
0.6163	Remote Similarity	NPC475604
0.6124	Remote Similarity	NPC103268
0.6073	Remote Similarity	NPC49195
0.6059	Remote Similarity	NPC188104
0.6038	Remote Similarity	NPC314930
0.6038	Remote Similarity	NPC214827
0.6021	Remote Similarity	NPC56058
0.6021	Remote Similarity	NPC522
0.6011	Remote Similarity	NPC474070
0.601	Remote Similarity	NPC132662
0.5978	Remote Similarity	NPC470824
0.5957	Remote Similarity	NPC14101
0.5953	Remote Similarity	NPC475024
0.5936	Remote Similarity	NPC475683
0.5936	Remote Similarity	NPC157194
0.5936	Remote Similarity	NPC474080
0.5936	Remote Similarity	NPC474102
0.5936	Remote Similarity	NPC474079
0.5936	Remote Similarity	NPC21449
0.5926	Remote Similarity	NPC268063
0.5926	Remote Similarity	NPC224609
0.5922	Remote Similarity	NPC197881
0.5915	Remote Similarity	NPC138562
0.5914	Remote Similarity	NPC315061
0.5909	Remote Similarity	NPC300315
0.5898	Remote Similarity	NPC315411
0.5892	Remote Similarity	NPC474069
0.5885	Remote Similarity	NPC231110
0.5882	Remote Similarity	NPC474064
0.5882	Remote Similarity	NPC474103
0.5882	Remote Similarity	NPC474068
0.5882	Remote Similarity	NPC82436
0.5882	Remote Similarity	NPC7817
0.5882	Remote Similarity	NPC475168
0.5877	Remote Similarity	NPC313421
0.5873	Remote Similarity	NPC252616
0.5873	Remote Similarity	NPC163147
0.5873	Remote Similarity	NPC32583
0.5873	Remote Similarity	NPC109498
0.5873	Remote Similarity	NPC45576
0.5873	Remote Similarity	NPC50274
0.5873	Remote Similarity	NPC61667
0.5873	Remote Similarity	NPC474090
0.5873	Remote Similarity	NPC154873
0.5871	Remote Similarity	NPC164228
0.5869	Remote Similarity	NPC182507
0.5855	Remote Similarity	NPC312887
0.5854	Remote Similarity	NPC238242
0.5845	Remote Similarity	NPC110602
0.5845	Remote Similarity	NPC75726
0.5845	Remote Similarity	NPC31385
0.5833	Remote Similarity	NPC127775
0.5833	Remote Similarity	NPC474538
0.582	Remote Similarity	NPC185665
0.582	Remote Similarity	NPC474094
0.582	Remote Similarity	NPC474067
0.582	Remote Similarity	NPC475737
0.5815	Remote Similarity	NPC476978
0.5789	Remote Similarity	NPC206724
0.5789	Remote Similarity	NPC474515
0.5789	Remote Similarity	NPC470902
0.5787	Remote Similarity	NPC34319
0.5775	Remote Similarity	NPC105717
0.5769	Remote Similarity	NPC478029
0.5765	Remote Similarity	NPC473886
0.5759	Remote Similarity	NPC161108
0.5753	Remote Similarity	NPC190329
0.5753	Remote Similarity	NPC262077
0.5751	Remote Similarity	NPC52587
0.575	Remote Similarity	NPC477462
0.5747	Remote Similarity	NPC46427
0.5735	Remote Similarity	NPC163055
0.5729	Remote Similarity	NPC202591
0.5729	Remote Similarity	NPC470507
0.5729	Remote Similarity	NPC212214
0.5728	Remote Similarity	NPC18487
0.5722	Remote Similarity	NPC83790
0.5722	Remote Similarity	NPC287401
0.5722	Remote Similarity	NPC128237
0.5721	Remote Similarity	NPC24594
0.5721	Remote Similarity	NPC472122
0.5721	Remote Similarity	NPC193761
0.5714	Remote Similarity	NPC222391
0.5714	Remote Similarity	NPC476118
0.5708	Remote Similarity	NPC162860
0.5708	Remote Similarity	NPC478158
0.5707	Remote Similarity	NPC256912
0.57	Remote Similarity	NPC329731
0.57	Remote Similarity	NPC4910
0.57	Remote Similarity	NPC134480
0.5699	Remote Similarity	NPC316008
0.5699	Remote Similarity	NPC313867
0.5699	Remote Similarity	NPC21126
0.5694	Remote Similarity	NPC143325
0.5692	Remote Similarity	NPC110129
0.5692	Remote Similarity	NPC201014
0.569	Remote Similarity	NPC252878
0.5685	Remote Similarity	NPC475554
0.5684	Remote Similarity	NPC478028
0.5683	Remote Similarity	NPC253987
0.5674	Remote Similarity	NPC475506
0.5673	Remote Similarity	NPC46413
0.5672	Remote Similarity	NPC473704
0.5672	Remote Similarity	NPC469938
0.5668	Remote Similarity	NPC314358
0.5654	Remote Similarity	NPC148592
0.5654	Remote Similarity	NPC286551
0.565	Remote Similarity	NPC273714
0.5648	Remote Similarity	NPC155143
0.5648	Remote Similarity	NPC477815
0.5645	Remote Similarity	NPC314388
0.5645	Remote Similarity	NPC315283
0.5637	Remote Similarity	NPC187827
0.5637	Remote Similarity	NPC472105
0.5636	Remote Similarity	NPC107077
0.5636	Remote Similarity	NPC223791
0.5631	Remote Similarity	NPC472294
0.5619	Remote Similarity	NPC313804
0.5619	Remote Similarity	NPC315804
0.5618	Remote Similarity	NPC151779
0.5616	Remote Similarity	NPC326575
0.5616	Remote Similarity	NPC54420
0.5616	Remote Similarity	NPC211997
0.5616	Remote Similarity	NPC323927
0.5616	Remote Similarity	NPC248454
0.5615	Remote Similarity	NPC322878
0.5615	Remote Similarity	NPC88121
0.5613	Remote Similarity	NPC184933
0.5613	Remote Similarity	NPC294693
0.5613	Remote Similarity	NPC59827
0.5611	Remote Similarity	NPC130309
0.5607	Remote Similarity	NPC473640
0.5602	Remote Similarity	NPC37548

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 NPC475330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	578
0.2-0.3	996
0.3-0.4	2384
0.4-0.5	4201
0.5-0.6	806
0.6-0.7	33
0.7-0.8	3
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
0.7323	Intermediate Similarity	NPD8260	Approved
0.7273	Intermediate Similarity	NPD8071	Approved
0.7258	Intermediate Similarity	NPD7977	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7806	Phase 2
0.6648	Remote Similarity	NPD5634	Approved
0.6548	Remote Similarity	NPD6349	Phase 1
0.6382	Remote Similarity	NPD2015	Discontinued
0.6308	Remote Similarity	NPD2957	Phase 2
0.6275	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6915	Approved
0.622	Remote Similarity	NPD6888	Discontinued
0.6214	Remote Similarity	NPD3469	Phase 3
0.6204	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD4949	Discontinued
0.6154	Remote Similarity	NPD924	Discontinued
0.615	Remote Similarity	NPD6092	Discontinued
0.6131	Remote Similarity	NPD1745	Approved
0.6121	Remote Similarity	NPD4741	Phase 3
0.6121	Remote Similarity	NPD4742	Phase 3
0.6108	Remote Similarity	NPD3575	Approved
0.6108	Remote Similarity	NPD3576	Approved
0.6099	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD2717	Phase 2
0.6095	Remote Similarity	NPD6308	Phase 1
0.6085	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4856	Approved
0.6071	Remote Similarity	NPD4855	Phase 1
0.6066	Remote Similarity	NPD5503	Approved
0.6066	Remote Similarity	NPD5502	Approved
0.6049	Remote Similarity	NPD8284	Discontinued
0.6029	Remote Similarity	NPD5828	Phase 2
0.6023	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3015	Discontinued
0.6019	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3759	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7496	Phase 2
0.598	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD649	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5596	Phase 2
0.5969	Remote Similarity	NPD647	Approved
0.5968	Remote Similarity	NPD1004	Phase 2
0.5968	Remote Similarity	NPD1005	Phase 2
0.5965	Remote Similarity	NPD4929	Approved
0.5965	Remote Similarity	NPD4930	Approved
0.5965	Remote Similarity	NPD4928	Approved
0.5956	Remote Similarity	NPD7711	Discontinued
0.5943	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6205	Discontinued
0.5918	Remote Similarity	NPD4650	Approved
0.5904	Remote Similarity	NPD3835	Phase 3
0.5904	Remote Similarity	NPD3833	Phase 3
0.5897	Remote Similarity	NPD7770	Phase 3
0.5897	Remote Similarity	NPD7133	Discontinued
0.5894	Remote Similarity	NPD7127	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD8272	Phase 2
0.5888	Remote Similarity	NPD754	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD6347	Phase 2
0.5885	Remote Similarity	NPD704	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD7104	Clinical (unspecified phase)
0.587	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6324	Phase 1
0.5833	Remote Similarity	NPD5439	Approved
0.5833	Remote Similarity	NPD5438	Approved
0.5823	Remote Similarity	NPD5435	Phase 1
0.582	Remote Similarity	NPD6907	Phase 2
0.5816	Remote Similarity	NPD7769	Phase 3
0.5812	Remote Similarity	NPD1597	Phase 1
0.5806	Remote Similarity	NPD4509	Discontinued
0.5799	Remote Similarity	NPD3907	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD3328	Phase 2
0.5797	Remote Similarity	NPD8063	Discontinued
0.5792	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD1218	Approved
0.5782	Remote Similarity	NPD1219	Approved
0.5782	Remote Similarity	NPD7490	Discontinued
0.5775	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD2543	Discontinued
0.5773	Remote Similarity	NPD5452	Phase 2
0.5773	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD5461	Discontinued
0.5765	Remote Similarity	NPD6360	Discontinued
0.5764	Remote Similarity	NPD8408	Discontinued
0.576	Remote Similarity	NPD8322	Phase 2
0.5754	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.575	Remote Similarity	NPD1260	Approved
0.5728	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD4557	Approved
0.5721	Remote Similarity	NPD5023	Discontinued
0.5714	Remote Similarity	NPD5140	Approved
0.5714	Remote Similarity	NPD7001	Phase 3
0.5714	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5138	Approved
0.5714	Remote Similarity	NPD5047	Clinical (unspecified phase)
0.57	Remote Similarity	NPD2749	Discontinued
0.5699	Remote Similarity	NPD6910	Phase 3
0.5694	Remote Similarity	NPD5144	Discontinued
0.5694	Remote Similarity	NPD8072	Approved
0.569	Remote Similarity	NPD2389	Approved
0.5687	Remote Similarity	NPD3396	Approved
0.5687	Remote Similarity	NPD3395	Approved
0.5682	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD2893	Phase 3
0.5676	Remote Similarity	NPD4331	Approved
0.5674	Remote Similarity	NPD1881	Approved
0.5673	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8107	Approved
0.5664	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD3487	Phase 1
0.5662	Remote Similarity	NPD7981	Discontinued
0.5659	Remote Similarity	NPD7928	Approved
0.5659	Remote Similarity	NPD7929	Approved
0.5652	Remote Similarity	NPD6170	Phase 2
0.565	Remote Similarity	NPD3848	Phase 2
0.5647	Remote Similarity	NPD8108	Approved
0.5646	Remote Similarity	NPD3474	Discovery
0.5645	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.564	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD6381	Phase 2
0.5635	Remote Similarity	NPD8129	Discovery
0.5634	Remote Similarity	NPD7021	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD9579	Approved
0.5631	Remote Similarity	NPD7483	Phase 2
0.5631	Remote Similarity	NPD7482	Phase 2
0.5625	Remote Similarity	NPD5663	Discontinued
0.5625	Remote Similarity	NPD5817	Discontinued
0.5622	Remote Similarity	NPD6139	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6911	Discontinued
0.5619	Remote Similarity	NPD6455	Phase 3
0.5616	Remote Similarity	NPD7834	Approved
0.5616	Remote Similarity	NPD4415	Approved
0.5616	Remote Similarity	NPD8122	Approved
0.5616	Remote Similarity	NPD8123	Approved
0.5612	Remote Similarity	NPD7738	Approved
0.5612	Remote Similarity	NPD7737	Approved
0.5607	Remote Similarity	NPD4470	Phase 2
0.5607	Remote Similarity	NPD7946	Pre-registration
0.5606	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD3279	Phase 2
0.5604	Remote Similarity	NPD5323	Approved
0.5604	Remote Similarity	NPD6227	Discontinued
0.56	Remote Similarity	NPD5523	Approved
0.56	Remote Similarity	NPD5524	Approved
0.56	Remote Similarity	NPD1976	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