NPASS Compound

Structure

NPC177362 OpenBabel07101719152D 52 58 0 0 1 0 0 0 0 0999 V2000 2.8472 -0.9930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2013 -2.6585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4915 4.7836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9831 3.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9777 -2.0689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7027 1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 0.4915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7027 0.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6621 1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5540 -3.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7027 -2.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4054 -2.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7027 -1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4054 -1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1081 2.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1821 -3.0304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7027 3.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2044 -2.9277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7027 2.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1081 0.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7027 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 -1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5435 -1.9280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5540 -1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5819 -2.1324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8513 -0.4915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9594 2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9594 1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7027 0.9831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.9492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8513 4.4237 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8513 -0.4915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8513 -1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8513 1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5540 -0.4915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4054 0.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8513 2.4576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8108 2.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 5.4068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4054 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4054 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8108 0.9831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5540 1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7027 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 2 0 0 0 0 2 26 1 0 0 0 0 3 41 1 0 0 0 0 4 41 1 0 0 0 0 7 44 1 0 0 0 0 9 50 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 27 2 0 0 0 0 14 27 1 0 0 0 0 15 16 2 0 0 0 0 15 28 1 0 0 0 0 16 31 1 0 0 0 0 17 20 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 18 34 1 0 0 0 0 19 21 1 0 0 0 0 19 35 1 0 0 0 0 20 42 1 0 0 0 0 21 43 1 0 0 0 0 22 44 1 0 0 0 0 23 28 2 0 0 0 0 23 32 1 0 0 0 0 24 30 1 0 0 0 0 24 33 1 0 0 0 0 25 36 1 0 0 0 0 25 42 1 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 26 1 6 0 0 0 29 37 1 0 0 0 0 30 37 1 0 0 0 0 30 45 1 6 0 0 0 31 32 2 0 0 0 0 31 46 1 0 0 0 0 32 50 1 0 0 0 0 33 38 1 0 0 0 0 33 51 1 6 0 0 0 34 41 1 0 0 0 0 34 43 1 1 0 0 0 35 41 1 0 0 0 0 35 47 1 1 0 0 0 36 45 1 6 0 0 0 36 52 1 0 0 0 0 37 42 1 1 0 0 0 38 43 1 1 0 0 0 38 44 1 0 0 0 0 39 48 2 0 0 0 0 39 52 1 0 0 0 0 40 49 2 0 0 0 0 40 51 1 0 0 0 0 42 5 1 1 0 0 0 43 6 1 1 0 0 0 44 45 1 6 0 0 0 45 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	712.43
Volume:	764.784
LogP:	8.182
LogD:	6.154
LogS:	-4.608
# Rotatable Bonds:	8
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.227
Synthetic Accessibility Score:	5.234
Fsp3:	0.644
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.2
MDCK Permeability:	2.012512595683802e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.252

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	101.6043930053711%
Volume Distribution (VD):	0.959
Pgp-substrate:	5.509104251861572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.441
CYP2C19-inhibitor:	0.149
CYP2C19-substrate:	0.795
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.105
CYP2D6-substrate:	0.77
CYP3A4-inhibitor:	0.422
CYP3A4-substrate:	0.582

ADMET: Excretion

Clearance (CL):	7.509
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.55
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.381
Carcinogencity:	0.008
Eye Corrosion:	0.004
Eye Irritation:	0.215
Respiratory Toxicity:	0.485

Download Data

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

Natural Product: NPC177362

Natural Product ID:	NPC177362
*Common Name:**	Ulmicin E
IUPAC Name:	[(1R,3aR,5S,5aR,5bR,7aR,9S,11aS,11bR,12R,13aR,13bR)-5-benzoyloxy-9-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-12-yl] 4-hydroxy-3-methoxybenzoate
Synonyms:	ulmicin E
Standard InCHIKey:	BXULOPKZYSOQMM-RWUMXVMBSA-N
Standard InCHI:	InChI=1S/C45H60O7/c1-26(2)29-17-20-42(5)25-36(52-39(48)27-13-11-10-12-14-27)45(8)30(37(29)42)24-33(51-40(49)28-15-16-31(46)32(23-28)50-9)38-43(6)21-19-35(47)41(3,4)34(43)18-22-44(38,45)7/h10-16,23,29-30,33-38,46-47H,1,17-22,24-25H2,2-9H3/t29-,30+,33+,34-,35-,36-,37+,38+,42+,43-,44+,45-/m0/s1
SMILES:	COc1cc(ccc1O)C(=O)O[C@@H]1C[C@@H]2[C@H]3[C@@H](CC[C@]3(C)C[C@@H]([C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O)C)C)OC(=O)c1ccccc1)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500710
PubChem CID:	21590546
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO2200.1	Ulmus davidiana	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277749]

☑ 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.	Activity	=	41.0	%	PMID[534731]

☑ 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 NPC177362 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	386
0.1-0.2	1423
0.2-0.3	2860
0.3-0.4	5381
0.4-0.5	9364
0.5-0.6	8877
0.6-0.7	8473
0.7-0.8	5609
0.8-0.85	224
0.85-0.9	87
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC266545
0.9937	High Similarity	NPC202428
0.9936	High Similarity	NPC200726
0.9268	High Similarity	NPC472803
0.9236	High Similarity	NPC105942
0.9236	High Similarity	NPC205392
0.9057	High Similarity	NPC62051
0.8987	High Similarity	NPC118033
0.8981	High Similarity	NPC279442
0.8931	High Similarity	NPC475579
0.8931	High Similarity	NPC124842
0.8931	High Similarity	NPC473773
0.8868	High Similarity	NPC475311
0.8868	High Similarity	NPC473579
0.8868	High Similarity	NPC473680
0.8868	High Similarity	NPC475454
0.8848	High Similarity	NPC100420
0.8841	High Similarity	NPC266365
0.8805	High Similarity	NPC470619
0.8805	High Similarity	NPC208785
0.8805	High Similarity	NPC470618
0.8805	High Similarity	NPC145527
0.8805	High Similarity	NPC327962
0.879	High Similarity	NPC66894
0.879	High Similarity	NPC8102
0.8742	High Similarity	NPC273358
0.8742	High Similarity	NPC298647
0.8735	High Similarity	NPC45943
0.8728	High Similarity	NPC473205
0.8728	High Similarity	NPC473776
0.8726	High Similarity	NPC235195
0.8726	High Similarity	NPC469683
0.8726	High Similarity	NPC19862
0.8696	High Similarity	NPC267091
0.8688	High Similarity	NPC142654
0.8679	High Similarity	NPC32017
0.8679	High Similarity	NPC96930
0.8662	High Similarity	NPC469615
0.8639	High Similarity	NPC21956
0.8634	High Similarity	NPC243891
0.8625	High Similarity	NPC292206
0.8614	High Similarity	NPC216916
0.8608	High Similarity	NPC271607
0.8608	High Similarity	NPC280717
0.8608	High Similarity	NPC307205
0.8599	High Similarity	NPC252133
0.8596	High Similarity	NPC316539
0.8596	High Similarity	NPC475299
0.8589	High Similarity	NPC469888
0.8588	High Similarity	NPC180768
0.8563	High Similarity	NPC188217
0.8562	High Similarity	NPC325032
0.8562	High Similarity	NPC477483
0.8553	High Similarity	NPC75295
0.8545	High Similarity	NPC296044
0.8545	High Similarity	NPC167098
0.8538	High Similarity	NPC100925
0.8538	High Similarity	NPC469773
0.8538	High Similarity	NPC469775
0.8538	High Similarity	NPC32723
0.8538	High Similarity	NPC469772
0.8538	High Similarity	NPC469778
0.8538	High Similarity	NPC295941
0.8538	High Similarity	NPC135334
0.8538	High Similarity	NPC469776
0.8538	High Similarity	NPC469777
0.8538	High Similarity	NPC469774
0.8537	High Similarity	NPC472807
0.8535	High Similarity	NPC35212
0.8523	High Similarity	NPC299855
0.8523	High Similarity	NPC96194
0.8521	High Similarity	NPC263212
0.8509	High Similarity	NPC98809
0.8509	High Similarity	NPC476394
0.8503	High Similarity	NPC469889
0.8503	High Similarity	NPC131905
0.8491	Intermediate Similarity	NPC53520
0.8488	Intermediate Similarity	NPC98583
0.8481	Intermediate Similarity	NPC469447
0.8481	Intermediate Similarity	NPC477873
0.8481	Intermediate Similarity	NPC310621
0.8475	Intermediate Similarity	NPC189704
0.8471	Intermediate Similarity	NPC473612
0.8471	Intermediate Similarity	NPC286809
0.8466	Intermediate Similarity	NPC48671
0.8457	Intermediate Similarity	NPC303989
0.8457	Intermediate Similarity	NPC474305
0.8452	Intermediate Similarity	NPC476371
0.8452	Intermediate Similarity	NPC145847
0.8452	Intermediate Similarity	NPC476372
0.8447	Intermediate Similarity	NPC472969
0.8447	Intermediate Similarity	NPC470757
0.8444	Intermediate Similarity	NPC476358
0.8443	Intermediate Similarity	NPC476373
0.8443	Intermediate Similarity	NPC24627
0.8439	Intermediate Similarity	NPC469438
0.8439	Intermediate Similarity	NPC469354
0.8438	Intermediate Similarity	NPC258856
0.8434	Intermediate Similarity	NPC143328
0.843	Intermediate Similarity	NPC65333
0.843	Intermediate Similarity	NPC100251
0.8428	Intermediate Similarity	NPC26045
0.8428	Intermediate Similarity	NPC473090
0.8428	Intermediate Similarity	NPC25491
0.8427	Intermediate Similarity	NPC475121
0.8427	Intermediate Similarity	NPC476067
0.8424	Intermediate Similarity	NPC180901
0.8424	Intermediate Similarity	NPC300757
0.8415	Intermediate Similarity	NPC131121
0.8405	Intermediate Similarity	NPC261659
0.8402	Intermediate Similarity	NPC161151
0.8402	Intermediate Similarity	NPC277618
0.8402	Intermediate Similarity	NPC100425
0.8402	Intermediate Similarity	NPC109990
0.84	Intermediate Similarity	NPC93685
0.84	Intermediate Similarity	NPC108191
0.8395	Intermediate Similarity	NPC474306
0.8395	Intermediate Similarity	NPC475848
0.8391	Intermediate Similarity	NPC469397
0.8385	Intermediate Similarity	NPC58752
0.8373	Intermediate Similarity	NPC470896
0.8373	Intermediate Similarity	NPC7059
0.8373	Intermediate Similarity	NPC473275
0.8365	Intermediate Similarity	NPC141817
0.8365	Intermediate Similarity	NPC176030
0.8365	Intermediate Similarity	NPC229218
0.8365	Intermediate Similarity	NPC192597
0.8365	Intermediate Similarity	NPC169214
0.8365	Intermediate Similarity	NPC235557
0.8354	Intermediate Similarity	NPC27518
0.8354	Intermediate Similarity	NPC304110
0.8353	Intermediate Similarity	NPC310572
0.8344	Intermediate Similarity	NPC248287
0.8344	Intermediate Similarity	NPC261322
0.8344	Intermediate Similarity	NPC234548
0.8343	Intermediate Similarity	NPC473445
0.8333	Intermediate Similarity	NPC185617
0.8333	Intermediate Similarity	NPC53889
0.8333	Intermediate Similarity	NPC79571
0.8324	Intermediate Similarity	NPC148185
0.8323	Intermediate Similarity	NPC226759
0.8323	Intermediate Similarity	NPC187205
0.8314	Intermediate Similarity	NPC186100
0.8314	Intermediate Similarity	NPC216403
0.8314	Intermediate Similarity	NPC41494
0.8313	Intermediate Similarity	NPC46161
0.8313	Intermediate Similarity	NPC471876
0.8313	Intermediate Similarity	NPC239608
0.8304	Intermediate Similarity	NPC43065
0.8304	Intermediate Similarity	NPC296558
0.8303	Intermediate Similarity	NPC65591
0.8303	Intermediate Similarity	NPC295646
0.8303	Intermediate Similarity	NPC178574
0.8294	Intermediate Similarity	NPC223006
0.8294	Intermediate Similarity	NPC272750
0.8294	Intermediate Similarity	NPC291977
0.8294	Intermediate Similarity	NPC173729
0.8294	Intermediate Similarity	NPC134047
0.8293	Intermediate Similarity	NPC119252
0.8286	Intermediate Similarity	NPC478050
0.8286	Intermediate Similarity	NPC79736
0.8286	Intermediate Similarity	NPC475054
0.8286	Intermediate Similarity	NPC67629
0.8286	Intermediate Similarity	NPC472723
0.8278	Intermediate Similarity	NPC71385
0.8278	Intermediate Similarity	NPC230670
0.8276	Intermediate Similarity	NPC195972
0.8276	Intermediate Similarity	NPC475197
0.8276	Intermediate Similarity	NPC473467
0.8274	Intermediate Similarity	NPC8389
0.8274	Intermediate Similarity	NPC471750
0.8274	Intermediate Similarity	NPC68619
0.8274	Intermediate Similarity	NPC179914
0.8274	Intermediate Similarity	NPC87317
0.8272	Intermediate Similarity	NPC191899
0.8272	Intermediate Similarity	NPC246229
0.8272	Intermediate Similarity	NPC474991
0.8266	Intermediate Similarity	NPC476365
0.8263	Intermediate Similarity	NPC478223
0.8263	Intermediate Similarity	NPC471968
0.8263	Intermediate Similarity	NPC213401
0.8253	Intermediate Similarity	NPC305710
0.8253	Intermediate Similarity	NPC25127
0.8246	Intermediate Similarity	NPC471788
0.8242	Intermediate Similarity	NPC75695
0.8242	Intermediate Similarity	NPC270268
0.8242	Intermediate Similarity	NPC294511
0.8242	Intermediate Similarity	NPC121615
0.8242	Intermediate Similarity	NPC476434
0.8239	Intermediate Similarity	NPC470035
0.8239	Intermediate Similarity	NPC469418
0.8239	Intermediate Similarity	NPC267549
0.8239	Intermediate Similarity	NPC29599
0.8239	Intermediate Similarity	NPC172311
0.8239	Intermediate Similarity	NPC100675
0.8239	Intermediate Similarity	NPC260300
0.8239	Intermediate Similarity	NPC326065
0.8235	Intermediate Similarity	NPC144557
0.8235	Intermediate Similarity	NPC476011
0.8235	Intermediate Similarity	NPC149389

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 NPC177362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	839
0.2-0.3	1686
0.3-0.4	2561
0.4-0.5	2101
0.5-0.6	1142
0.6-0.7	404
0.7-0.8	78
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8614	High Similarity	NPD8127	Discontinued
0.84	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD7685	Pre-registration
0.8362	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD8166	Discontinued
0.8187	Intermediate Similarity	NPD4628	Phase 3
0.816	Intermediate Similarity	NPD6273	Approved
0.8155	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7458	Discontinued
0.8103	Intermediate Similarity	NPD5844	Phase 1
0.8046	Intermediate Similarity	NPD7228	Approved
0.8011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.7953	Intermediate Similarity	NPD6234	Discontinued
0.7919	Intermediate Similarity	NPD6232	Discontinued
0.7877	Intermediate Similarity	NPD8313	Approved
0.7877	Intermediate Similarity	NPD8312	Approved
0.787	Intermediate Similarity	NPD37	Approved
0.7853	Intermediate Similarity	NPD7003	Approved
0.7836	Intermediate Similarity	NPD4965	Approved
0.7836	Intermediate Similarity	NPD4967	Phase 2
0.7836	Intermediate Similarity	NPD4966	Approved
0.7829	Intermediate Similarity	NPD6166	Phase 2
0.7829	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD1934	Approved
0.7759	Intermediate Similarity	NPD7199	Phase 2
0.7753	Intermediate Similarity	NPD7074	Phase 3
0.7747	Intermediate Similarity	NPD8434	Phase 2
0.774	Intermediate Similarity	NPD3818	Discontinued
0.7719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD1465	Phase 2
0.7697	Intermediate Similarity	NPD6190	Approved
0.7697	Intermediate Similarity	NPD7054	Approved
0.7654	Intermediate Similarity	NPD7472	Approved
0.763	Intermediate Similarity	NPD3882	Suspended
0.7625	Intermediate Similarity	NPD3620	Phase 2
0.7625	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2801	Approved
0.76	Intermediate Similarity	NPD5494	Approved
0.7576	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7240	Approved
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7552	Intermediate Similarity	NPD7497	Discontinued
0.7544	Intermediate Similarity	NPD4380	Phase 2
0.753	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4110	Phase 3
0.7527	Intermediate Similarity	NPD7808	Phase 3
0.7527	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5761	Phase 2
0.7514	Intermediate Similarity	NPD7819	Suspended
0.7514	Intermediate Similarity	NPD5760	Phase 2
0.7486	Intermediate Similarity	NPD7075	Discontinued
0.7473	Intermediate Similarity	NPD7251	Discontinued
0.7471	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3817	Phase 2
0.7469	Intermediate Similarity	NPD230	Phase 1
0.7442	Intermediate Similarity	NPD7028	Phase 2
0.744	Intermediate Similarity	NPD7236	Approved
0.7429	Intermediate Similarity	NPD7768	Phase 2
0.7421	Intermediate Similarity	NPD9494	Approved
0.7418	Intermediate Similarity	NPD6797	Phase 2
0.7414	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8455	Phase 2
0.7399	Intermediate Similarity	NPD6386	Approved
0.7399	Intermediate Similarity	NPD6385	Approved
0.7391	Intermediate Similarity	NPD3764	Approved
0.7384	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3226	Approved
0.7371	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6355	Discontinued
0.736	Intermediate Similarity	NPD8151	Discontinued
0.736	Intermediate Similarity	NPD6959	Discontinued
0.7353	Intermediate Similarity	NPD2533	Approved
0.7353	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2534	Approved
0.7353	Intermediate Similarity	NPD2532	Approved
0.7349	Intermediate Similarity	NPD5762	Approved
0.7349	Intermediate Similarity	NPD5763	Approved
0.7349	Intermediate Similarity	NPD7266	Discontinued
0.7346	Intermediate Similarity	NPD6663	Approved
0.7346	Intermediate Similarity	NPD8032	Phase 2
0.7341	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5736	Approved
0.7308	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4140	Approved
0.7294	Intermediate Similarity	NPD1511	Approved
0.7289	Intermediate Similarity	NPD2935	Discontinued
0.7288	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6764	Approved
0.7283	Intermediate Similarity	NPD6765	Approved
0.7282	Intermediate Similarity	NPD7435	Discontinued
0.7282	Intermediate Similarity	NPD7680	Approved
0.7257	Intermediate Similarity	NPD6801	Discontinued
0.7254	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7239	Suspended
0.7222	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3750	Approved
0.7209	Intermediate Similarity	NPD1512	Approved
0.7202	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7411	Suspended
0.7189	Intermediate Similarity	NPD7038	Approved
0.7189	Intermediate Similarity	NPD7039	Approved
0.7189	Intermediate Similarity	NPD6559	Discontinued
0.7175	Intermediate Similarity	NPD5402	Approved
0.717	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7097	Phase 1
0.7166	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7799	Discontinued
0.7158	Intermediate Similarity	NPD7177	Discontinued
0.7157	Intermediate Similarity	NPD7870	Phase 2
0.7157	Intermediate Similarity	NPD7871	Phase 2
0.7152	Intermediate Similarity	NPD5735	Approved
0.715	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7128	Intermediate Similarity	NPD6785	Approved
0.7128	Intermediate Similarity	NPD6784	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7126	Intermediate Similarity	NPD2799	Discontinued
0.7117	Intermediate Similarity	NPD7095	Approved
0.7107	Intermediate Similarity	NPD7696	Phase 3
0.7107	Intermediate Similarity	NPD1608	Approved
0.7107	Intermediate Similarity	NPD7697	Approved
0.7107	Intermediate Similarity	NPD7698	Approved
0.7102	Intermediate Similarity	NPD6873	Phase 2
0.7095	Intermediate Similarity	NPD3749	Approved
0.7093	Intermediate Similarity	NPD6799	Approved
0.7091	Intermediate Similarity	NPD4060	Phase 1
0.7088	Intermediate Similarity	NPD5242	Approved
0.7079	Intermediate Similarity	NPD5978	Approved
0.7079	Intermediate Similarity	NPD5977	Approved
0.7079	Intermediate Similarity	NPD5353	Approved
0.7073	Intermediate Similarity	NPD6798	Discontinued
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7071	Intermediate Similarity	NPD8319	Approved
0.7065	Intermediate Similarity	NPD3751	Discontinued
0.7059	Intermediate Similarity	NPD6674	Discontinued
0.7052	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7701	Phase 2
0.7048	Intermediate Similarity	NPD447	Suspended
0.7033	Intermediate Similarity	NPD7229	Phase 3
0.7033	Intermediate Similarity	NPD3787	Discontinued
0.703	Intermediate Similarity	NPD7783	Phase 2
0.703	Intermediate Similarity	NPD7801	Approved
0.703	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7033	Discontinued
0.7024	Intermediate Similarity	NPD1510	Phase 2
0.7019	Intermediate Similarity	NPD1283	Approved
0.7019	Intermediate Similarity	NPD1876	Approved
0.7012	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6653	Approved
0.7006	Intermediate Similarity	NPD9545	Approved
0.7	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7831	Phase 2
0.7	Intermediate Similarity	NPD7833	Phase 2
0.7	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD1549	Phase 2
0.6994	Remote Similarity	NPD2861	Phase 2
0.6989	Remote Similarity	NPD3455	Phase 2
0.6988	Remote Similarity	NPD2979	Phase 3
0.6988	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1613	Approved
0.6982	Remote Similarity	NPD2438	Suspended
0.6982	Remote Similarity	NPD5404	Approved
0.6982	Remote Similarity	NPD5405	Approved
0.6982	Remote Similarity	NPD5406	Approved
0.6982	Remote Similarity	NPD6099	Approved
0.6982	Remote Similarity	NPD6100	Approved
0.6982	Remote Similarity	NPD5408	Approved
0.6979	Remote Similarity	NPD2488	Approved
0.6979	Remote Similarity	NPD2490	Approved
0.6971	Remote Similarity	NPD5403	Approved
0.697	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6823	Phase 2
0.6961	Remote Similarity	NPD919	Approved
0.6954	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6005	Phase 3
0.6941	Remote Similarity	NPD6004	Phase 3
0.6941	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6002	Phase 3
0.6941	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7700	Phase 2
0.6939	Remote Similarity	NPD7699	Phase 2
0.6932	Remote Similarity	NPD1653	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