NPASS Compound

Structure

NPC266545 OpenBabel07101718322D 55 61 0 0 1 0 0 0 0 0999 V2000 -2.8496 0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2039 2.6607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4919 -4.7875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9839 -3.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9785 2.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7041 -1.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 -0.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7041 -0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6685 -1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 4.4274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2603 -2.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4082 1.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1123 -2.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4082 2.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1830 3.0330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 -2.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7041 -3.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2046 2.9301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7041 -2.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 -1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1123 -0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7041 1.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7041 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5456 1.9296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2603 -1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5562 1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5832 2.1341 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8521 0.4919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9644 -2.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5562 3.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9644 -1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7041 2.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7041 -0.9839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.9516 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8521 -4.4274 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8521 0.4919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8521 1.4758 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8521 -1.4758 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4082 -0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5562 0.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8521 -2.4597 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9839 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 -6.8165 -2.9516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5562 4.4274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8521 -5.4113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4082 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4082 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8165 -0.9839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 3.4435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5562 -1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7041 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 2 0 0 0 0 2 25 1 0 0 0 0 3 42 1 0 0 0 0 4 42 1 0 0 0 0 7 45 1 0 0 0 0 9 52 1 0 0 0 0 10 53 1 0 0 0 0 11 13 2 0 0 0 0 11 26 1 0 0 0 0 12 14 2 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 31 1 0 0 0 0 15 18 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 16 35 1 0 0 0 0 17 19 1 0 0 0 0 17 36 1 0 0 0 0 18 43 1 0 0 0 0 19 44 1 0 0 0 0 20 45 1 0 0 0 0 21 26 2 0 0 0 0 21 32 1 0 0 0 0 22 27 2 0 0 0 0 22 33 1 0 0 0 0 23 29 1 0 0 0 0 23 34 1 0 0 0 0 24 37 1 0 0 0 0 24 43 1 0 0 0 0 26 40 1 0 0 0 0 27 41 1 0 0 0 0 28 25 1 6 0 0 0 28 38 1 0 0 0 0 29 38 1 0 0 0 0 29 46 1 6 0 0 0 30 32 2 0 0 0 0 30 47 1 0 0 0 0 31 33 2 0 0 0 0 31 48 1 0 0 0 0 32 52 1 0 0 0 0 33 53 1 0 0 0 0 34 39 1 0 0 0 0 34 54 1 6 0 0 0 35 42 1 0 0 0 0 35 44 1 1 0 0 0 36 42 1 0 0 0 0 36 49 1 1 0 0 0 37 46 1 6 0 0 0 37 55 1 0 0 0 0 38 43 1 1 0 0 0 39 44 1 1 0 0 0 39 45 1 0 0 0 0 40 50 2 0 0 0 0 40 54 1 0 0 0 0 41 51 2 0 0 0 0 41 55 1 0 0 0 0 43 5 1 1 0 0 0 44 6 1 1 0 0 0 45 46 1 6 0 0 0 46 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	758.44
Volume:	799.66
LogP:	7.855
LogD:	5.887
LogS:	-3.99
# Rotatable Bonds:	9
TPSA:	131.75
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.187
Synthetic Accessibility Score:	5.368
Fsp3:	0.652
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:	-5.223
MDCK Permeability:	1.6837822840898298e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.366

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	100.07154846191406%
Volume Distribution (VD):	0.56
Pgp-substrate:	7.533830642700195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.86
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.152
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.161
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.578

ADMET: Excretion

Clearance (CL):	7.52
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.521
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.216
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.408
Carcinogencity:	0.004
Eye Corrosion:	0.004
Eye Irritation:	0.243
Respiratory Toxicity:	0.505

Download Data

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

Natural Product: NPC266545

Natural Product ID:	NPC266545
*Common Name:**	Ulmicin D
IUPAC Name:	[(1R,3aR,5S,5aR,5bR,7aR,9S,11aS,11bR,12R,13aR,13bR)-9-hydroxy-5-(4-hydroxy-3-methoxybenzoyl)oxy-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 D
Standard InCHIKey:	KXJAZRZJROOYLF-UJHKYAERSA-N
Standard InCHI:	InChI=1S/C46H62O9/c1-25(2)28-15-18-43(5)24-37(55-41(51)27-12-14-31(48)33(22-27)53-10)46(8)29(38(28)43)23-34(54-40(50)26-11-13-30(47)32(21-26)52-9)39-44(6)19-17-36(49)42(3,4)35(44)16-20-45(39,46)7/h11-14,21-22,28-29,34-39,47-49H,1,15-20,23-24H2,2-10H3/t28-,29+,34+,35-,36-,37-,38+,39+,43+,44-,45+,46-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)C[C@@H]([C@]3(C)[C@H](C[C@H]([C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)OC(=O)c3ccc(c(c3)OC)O)[C@@H]12)OC(=O)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444904
PubChem CID:	21590545
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	=	44.2	%	PMID[464530]

☑ 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 NPC266545 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	389
0.1-0.2	1423
0.2-0.3	2899
0.3-0.4	5394
0.4-0.5	9352
0.5-0.6	8892
0.6-0.7	8440
0.7-0.8	5571
0.8-0.85	231
0.85-0.9	91
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202428
0.9937	High Similarity	NPC177362
0.9873	High Similarity	NPC200726
0.9329	High Similarity	NPC472803
0.9177	High Similarity	NPC205392
0.9177	High Similarity	NPC105942
0.9	High Similarity	NPC62051
0.8931	High Similarity	NPC118033
0.8924	High Similarity	NPC279442
0.8909	High Similarity	NPC100420
0.8902	High Similarity	NPC266365
0.8875	High Similarity	NPC124842
0.8875	High Similarity	NPC475579
0.8875	High Similarity	NPC473773
0.8868	High Similarity	NPC327962
0.8812	High Similarity	NPC475311
0.8812	High Similarity	NPC473579
0.8812	High Similarity	NPC475454
0.8812	High Similarity	NPC473680
0.8795	High Similarity	NPC45943
0.8786	High Similarity	NPC473205
0.8786	High Similarity	NPC473776
0.8758	High Similarity	NPC267091
0.875	High Similarity	NPC145527
0.875	High Similarity	NPC470618
0.875	High Similarity	NPC208785
0.875	High Similarity	NPC470619
0.8734	High Similarity	NPC66894
0.8734	High Similarity	NPC8102
0.8698	High Similarity	NPC21956
0.8696	High Similarity	NPC243891
0.8688	High Similarity	NPC273358
0.8688	High Similarity	NPC298647
0.8675	High Similarity	NPC216916
0.8671	High Similarity	NPC469683
0.8671	High Similarity	NPC235195
0.8671	High Similarity	NPC19862
0.8655	High Similarity	NPC316539
0.8652	High Similarity	NPC475299
0.865	High Similarity	NPC469888
0.8647	High Similarity	NPC180768
0.8634	High Similarity	NPC142654
0.8625	High Similarity	NPC32017
0.8625	High Similarity	NPC96930
0.8621	High Similarity	NPC188217
0.8608	High Similarity	NPC469615
0.8598	High Similarity	NPC472807
0.8596	High Similarity	NPC469775
0.8596	High Similarity	NPC469772
0.8596	High Similarity	NPC100925
0.8596	High Similarity	NPC469773
0.8596	High Similarity	NPC32723
0.8596	High Similarity	NPC469774
0.8596	High Similarity	NPC469778
0.8596	High Similarity	NPC135334
0.8596	High Similarity	NPC469776
0.8596	High Similarity	NPC295941
0.8596	High Similarity	NPC469777
0.858	High Similarity	NPC299855
0.858	High Similarity	NPC96194
0.8571	High Similarity	NPC292206
0.8563	High Similarity	NPC469889
0.8553	High Similarity	NPC307205
0.8553	High Similarity	NPC53520
0.8553	High Similarity	NPC280717
0.8553	High Similarity	NPC271607
0.8547	High Similarity	NPC98583
0.8544	High Similarity	NPC252133
0.8531	High Similarity	NPC189704
0.8529	High Similarity	NPC286809
0.8512	High Similarity	NPC476372
0.8512	High Similarity	NPC476371
0.8512	High Similarity	NPC145847
0.8509	High Similarity	NPC472969
0.8509	High Similarity	NPC325032
0.8509	High Similarity	NPC477483
0.8503	High Similarity	NPC24627
0.8503	High Similarity	NPC476373
0.85	High Similarity	NPC75295
0.85	High Similarity	NPC476358
0.8497	Intermediate Similarity	NPC469438
0.8497	Intermediate Similarity	NPC469354
0.8494	Intermediate Similarity	NPC167098
0.8494	Intermediate Similarity	NPC296044
0.8488	Intermediate Similarity	NPC100251
0.8488	Intermediate Similarity	NPC65333
0.8483	Intermediate Similarity	NPC475121
0.8483	Intermediate Similarity	NPC476067
0.8481	Intermediate Similarity	NPC35212
0.8471	Intermediate Similarity	NPC263212
0.8462	Intermediate Similarity	NPC100425
0.8462	Intermediate Similarity	NPC109990
0.8462	Intermediate Similarity	NPC161151
0.8457	Intermediate Similarity	NPC476394
0.8457	Intermediate Similarity	NPC93685
0.8457	Intermediate Similarity	NPC98809
0.8457	Intermediate Similarity	NPC108191
0.8452	Intermediate Similarity	NPC131905
0.8448	Intermediate Similarity	NPC469397
0.8434	Intermediate Similarity	NPC470896
0.8434	Intermediate Similarity	NPC473275
0.8428	Intermediate Similarity	NPC310621
0.8428	Intermediate Similarity	NPC477873
0.8428	Intermediate Similarity	NPC469447
0.8418	Intermediate Similarity	NPC473612
0.8415	Intermediate Similarity	NPC48671
0.8405	Intermediate Similarity	NPC474305
0.8405	Intermediate Similarity	NPC303989
0.8402	Intermediate Similarity	NPC473445
0.8395	Intermediate Similarity	NPC470757
0.8393	Intermediate Similarity	NPC53889
0.8385	Intermediate Similarity	NPC258856
0.8383	Intermediate Similarity	NPC143328
0.8383	Intermediate Similarity	NPC187205
0.8383	Intermediate Similarity	NPC226759
0.8382	Intermediate Similarity	NPC148185
0.8375	Intermediate Similarity	NPC471876
0.8375	Intermediate Similarity	NPC26045
0.8375	Intermediate Similarity	NPC473090
0.8375	Intermediate Similarity	NPC25491
0.8373	Intermediate Similarity	NPC180901
0.8373	Intermediate Similarity	NPC300757
0.8372	Intermediate Similarity	NPC186100
0.8372	Intermediate Similarity	NPC41494
0.8372	Intermediate Similarity	NPC216403
0.8364	Intermediate Similarity	NPC178574
0.8364	Intermediate Similarity	NPC131121
0.8364	Intermediate Similarity	NPC65591
0.8363	Intermediate Similarity	NPC43065
0.8354	Intermediate Similarity	NPC261659
0.8354	Intermediate Similarity	NPC119252
0.8353	Intermediate Similarity	NPC291977
0.8353	Intermediate Similarity	NPC223006
0.8353	Intermediate Similarity	NPC272750
0.8353	Intermediate Similarity	NPC277618
0.8353	Intermediate Similarity	NPC173729
0.8353	Intermediate Similarity	NPC134047
0.8344	Intermediate Similarity	NPC474306
0.8344	Intermediate Similarity	NPC475848
0.8343	Intermediate Similarity	NPC79736
0.8343	Intermediate Similarity	NPC475054
0.8343	Intermediate Similarity	NPC472723
0.8343	Intermediate Similarity	NPC67629
0.8333	Intermediate Similarity	NPC473467
0.8333	Intermediate Similarity	NPC87317
0.8333	Intermediate Similarity	NPC195972
0.8333	Intermediate Similarity	NPC471750
0.8333	Intermediate Similarity	NPC71385
0.8333	Intermediate Similarity	NPC230670
0.8333	Intermediate Similarity	NPC58752
0.8333	Intermediate Similarity	NPC179914
0.8333	Intermediate Similarity	NPC475197
0.8324	Intermediate Similarity	NPC476365
0.8323	Intermediate Similarity	NPC7059
0.8313	Intermediate Similarity	NPC235557
0.8313	Intermediate Similarity	NPC169214
0.8313	Intermediate Similarity	NPC176030
0.8313	Intermediate Similarity	NPC141817
0.8313	Intermediate Similarity	NPC229218
0.8313	Intermediate Similarity	NPC192597
0.8304	Intermediate Similarity	NPC471788
0.8304	Intermediate Similarity	NPC310572
0.8303	Intermediate Similarity	NPC75695
0.8303	Intermediate Similarity	NPC476434
0.8303	Intermediate Similarity	NPC270268
0.8302	Intermediate Similarity	NPC27518
0.8302	Intermediate Similarity	NPC304110
0.8295	Intermediate Similarity	NPC267549
0.8295	Intermediate Similarity	NPC260300
0.8295	Intermediate Similarity	NPC469418
0.8294	Intermediate Similarity	NPC476011
0.8294	Intermediate Similarity	NPC144557
0.8294	Intermediate Similarity	NPC149389
0.8294	Intermediate Similarity	NPC42797
0.8293	Intermediate Similarity	NPC261322
0.8291	Intermediate Similarity	NPC234548
0.8291	Intermediate Similarity	NPC248287
0.8287	Intermediate Similarity	NPC112708
0.8284	Intermediate Similarity	NPC24164
0.8284	Intermediate Similarity	NPC472962
0.8284	Intermediate Similarity	NPC472961
0.8284	Intermediate Similarity	NPC79571
0.8284	Intermediate Similarity	NPC185617
0.8274	Intermediate Similarity	NPC133984
0.8274	Intermediate Similarity	NPC114179
0.8274	Intermediate Similarity	NPC471878
0.8274	Intermediate Similarity	NPC68324
0.8274	Intermediate Similarity	NPC38779
0.8274	Intermediate Similarity	NPC156818
0.8274	Intermediate Similarity	NPC289322
0.8274	Intermediate Similarity	NPC160512
0.8274	Intermediate Similarity	NPC268602
0.8263	Intermediate Similarity	NPC145425
0.8263	Intermediate Similarity	NPC203757
0.8261	Intermediate Similarity	NPC46161
0.8261	Intermediate Similarity	NPC239608
0.8256	Intermediate Similarity	NPC296558
0.8256	Intermediate Similarity	NPC469419
0.8253	Intermediate Similarity	NPC115203
0.8253	Intermediate Similarity	NPC295646

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 NPC266545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	844
0.2-0.3	1701
0.3-0.4	2573
0.4-0.5	2099
0.5-0.6	1130
0.6-0.7	390
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
0.8675	High Similarity	NPD8127	Discontinued
0.8457	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7685	Pre-registration
0.8418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD8166	Discontinued
0.8214	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD4628	Phase 3
0.811	Intermediate Similarity	NPD6273	Approved
0.8103	Intermediate Similarity	NPD7228	Approved
0.8072	Intermediate Similarity	NPD7458	Discontinued
0.8068	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD5844	Phase 1
0.8046	Intermediate Similarity	NPD7473	Discontinued
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.7977	Intermediate Similarity	NPD6232	Discontinued
0.7933	Intermediate Similarity	NPD8313	Approved
0.7933	Intermediate Similarity	NPD8312	Approved
0.7929	Intermediate Similarity	NPD37	Approved
0.7895	Intermediate Similarity	NPD4966	Approved
0.7895	Intermediate Similarity	NPD4967	Phase 2
0.7895	Intermediate Similarity	NPD4965	Approved
0.7886	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6166	Phase 2
0.7826	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7199	Phase 2
0.7809	Intermediate Similarity	NPD7074	Phase 3
0.7805	Intermediate Similarity	NPD7003	Approved
0.7802	Intermediate Similarity	NPD8434	Phase 2
0.7797	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6190	Approved
0.7753	Intermediate Similarity	NPD7054	Approved
0.7725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD1934	Approved
0.7709	Intermediate Similarity	NPD7472	Approved
0.7674	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7240	Approved
0.7609	Intermediate Similarity	NPD8150	Discontinued
0.7602	Intermediate Similarity	NPD4380	Phase 2
0.7586	Intermediate Similarity	NPD3882	Suspended
0.7582	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7808	Phase 3
0.7578	Intermediate Similarity	NPD3620	Phase 2
0.7578	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD2801	Approved
0.7572	Intermediate Similarity	NPD7819	Suspended
0.7557	Intermediate Similarity	NPD5494	Approved
0.7543	Intermediate Similarity	NPD7075	Discontinued
0.753	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3817	Phase 2
0.7529	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7251	Discontinued
0.7513	Intermediate Similarity	NPD7497	Discontinued
0.7485	Intermediate Similarity	NPD4110	Phase 3
0.7485	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6797	Phase 2
0.7471	Intermediate Similarity	NPD5761	Phase 2
0.7471	Intermediate Similarity	NPD5760	Phase 2
0.7471	Intermediate Similarity	NPD8455	Phase 2
0.7442	Intermediate Similarity	NPD3226	Approved
0.7429	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD230	Phase 1
0.7416	Intermediate Similarity	NPD6959	Discontinued
0.7412	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD8151	Discontinued
0.741	Intermediate Similarity	NPD7266	Discontinued
0.7399	Intermediate Similarity	NPD7028	Phase 2
0.7396	Intermediate Similarity	NPD7236	Approved
0.7389	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7768	Phase 2
0.7375	Intermediate Similarity	NPD9494	Approved
0.7371	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6385	Approved
0.7356	Intermediate Similarity	NPD6386	Approved
0.7346	Intermediate Similarity	NPD3764	Approved
0.7345	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7680	Approved
0.7333	Intermediate Similarity	NPD7435	Discontinued
0.7317	Intermediate Similarity	NPD6355	Discontinued
0.7314	Intermediate Similarity	NPD6801	Discontinued
0.731	Intermediate Similarity	NPD2533	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD2532	Approved
0.7306	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5762	Approved
0.7305	Intermediate Similarity	NPD5763	Approved
0.7301	Intermediate Similarity	NPD8032	Phase 2
0.7301	Intermediate Similarity	NPD6663	Approved
0.7299	Intermediate Similarity	NPD6599	Discontinued
0.7283	Intermediate Similarity	NPD7239	Suspended
0.7267	Intermediate Similarity	NPD5736	Approved
0.7257	Intermediate Similarity	NPD7411	Suspended
0.7256	Intermediate Similarity	NPD4140	Approved
0.7251	Intermediate Similarity	NPD1511	Approved
0.7246	Intermediate Similarity	NPD2935	Discontinued
0.7243	Intermediate Similarity	NPD6764	Approved
0.7243	Intermediate Similarity	NPD6559	Discontinued
0.7243	Intermediate Similarity	NPD6765	Approved
0.7232	Intermediate Similarity	NPD5402	Approved
0.7229	Intermediate Similarity	NPD7097	Phase 1
0.7213	Intermediate Similarity	NPD7799	Discontinued
0.7208	Intermediate Similarity	NPD7870	Phase 2
0.7208	Intermediate Similarity	NPD7871	Phase 2
0.72	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7874	Approved
0.7179	Intermediate Similarity	NPD6782	Approved
0.7179	Intermediate Similarity	NPD6779	Approved
0.7179	Intermediate Similarity	NPD6777	Approved
0.7179	Intermediate Similarity	NPD6776	Approved
0.7179	Intermediate Similarity	NPD6778	Approved
0.7179	Intermediate Similarity	NPD6781	Approved
0.7179	Intermediate Similarity	NPD6780	Approved
0.7178	Intermediate Similarity	NPD3027	Phase 3
0.7176	Intermediate Similarity	NPD3750	Approved
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1512	Approved
0.716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7698	Approved
0.7157	Intermediate Similarity	NPD7697	Approved
0.7157	Intermediate Similarity	NPD7696	Phase 3
0.7151	Intermediate Similarity	NPD7038	Approved
0.7151	Intermediate Similarity	NPD7039	Approved
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8319	Approved
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.712	Intermediate Similarity	NPD7177	Discontinued
0.7108	Intermediate Similarity	NPD5735	Approved
0.7101	Intermediate Similarity	NPD2346	Discontinued
0.71	Intermediate Similarity	NPD7701	Phase 2
0.709	Intermediate Similarity	NPD6784	Approved
0.709	Intermediate Similarity	NPD6785	Approved
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.7079	Intermediate Similarity	NPD7801	Approved
0.7079	Intermediate Similarity	NPD7783	Phase 2
0.7079	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7095	Approved
0.7063	Intermediate Similarity	NPD1608	Approved
0.7062	Intermediate Similarity	NPD6873	Phase 2
0.7056	Intermediate Similarity	NPD3749	Approved
0.7052	Intermediate Similarity	NPD6799	Approved
0.7049	Intermediate Similarity	NPD5242	Approved
0.7048	Intermediate Similarity	NPD4060	Phase 1
0.7041	Intermediate Similarity	NPD2438	Suspended
0.7039	Intermediate Similarity	NPD5978	Approved
0.7039	Intermediate Similarity	NPD5977	Approved
0.7039	Intermediate Similarity	NPD5353	Approved
0.703	Intermediate Similarity	NPD6798	Discontinued
0.7029	Intermediate Similarity	NPD5403	Approved
0.7027	Intermediate Similarity	NPD3751	Discontinued
0.702	Intermediate Similarity	NPD6823	Phase 2
0.7018	Intermediate Similarity	NPD6674	Discontinued
0.7011	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD447	Suspended
0.6995	Remote Similarity	NPD7229	Phase 3
0.6995	Remote Similarity	NPD3787	Discontinued
0.699	Remote Similarity	NPD7699	Phase 2
0.699	Remote Similarity	NPD7700	Phase 2
0.6989	Remote Similarity	NPD1653	Approved
0.6982	Remote Similarity	NPD1510	Phase 2
0.6982	Remote Similarity	NPD7033	Discontinued
0.6975	Remote Similarity	NPD1876	Approved
0.6975	Remote Similarity	NPD1283	Approved
0.697	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6653	Approved
0.6962	Remote Similarity	NPD9545	Approved
0.6961	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7833	Phase 2
0.6961	Remote Similarity	NPD7831	Phase 2
0.6959	Remote Similarity	NPD1549	Phase 2
0.6957	Remote Similarity	NPD3972	Approved
0.6954	Remote Similarity	NPD7390	Discontinued
0.6952	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2861	Phase 2
0.6949	Remote Similarity	NPD3455	Phase 2
0.6946	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2979	Phase 3
0.6946	Remote Similarity	NPD1613	Approved
0.6943	Remote Similarity	NPD2488	Approved
0.6943	Remote Similarity	NPD2490	Approved
0.6941	Remote Similarity	NPD5404	Approved
0.6941	Remote Similarity	NPD5405	Approved
0.6941	Remote Similarity	NPD5406	Approved
0.6941	Remote Similarity	NPD6099	Approved
0.6941	Remote Similarity	NPD6100	Approved
0.6941	Remote Similarity	NPD5408	Approved
0.6938	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD919	Approved
0.6923	Remote Similarity	NPD6535	Approved
0.6923	Remote Similarity	NPD6534	Approved
0.6914	Remote Similarity	NPD5401	Approved
0.6906	Remote Similarity	NPD7057	Phase 3

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