NPASS Compound

Structure

NPC207738 OpenBabel07101718192D 75 84 0 0 1 0 0 0 0 0999 V2000 -9.1444 5.3727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1891 -3.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2648 -2.9023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9900 2.2323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0028 2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8373 -0.6593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0741 1.3589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0148 0.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5996 -1.0754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2205 -0.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2524 1.4032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0832 0.3094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4623 -0.0368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6315 1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5361 -1.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6103 0.3646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9367 -1.6313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5920 -3.4602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6425 0.8923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3756 1.4498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1296 4.3855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0106 -0.7108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6315 -1.0570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.6278 -0.0948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7445 -2.9539 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5133 0.9690 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8627 1.0386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2312 -0.0184 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2312 0.0184 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0939 1.0202 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7354 -2.2116 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9771 3.8792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7655 -0.5756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8823 -3.4346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4986 -0.0181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0348 -2.9283 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9623 2.8921 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6363 -0.4989 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9180 -0.0693 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0496 -1.9412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1001 2.4113 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7888 0.0075 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9328 0.9179 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9118 -1.4604 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2526 2.9177 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8036 0.9946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2290 -0.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0274 -2.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4836 1.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8521 0.3278 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6209 0.3462 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 1.2418 -0.6924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5772 -4.4473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4753 -0.6012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0786 0.5248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8394 4.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7508 -1.5627 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8675 -4.4218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3461 -0.5244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1725 -3.4091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8098 2.3857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6215 -1.4860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0558 -0.5500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2021 -1.4348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8093 0.1063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7951 1.3986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3904 2.4369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2674 3.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7593 -1.9668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6659 1.4754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9561 1.5009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5341 -1.6313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0853 1.4242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9266 -0.4733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 48 1 0 0 0 0 3 48 1 0 0 0 0 4 49 1 0 0 0 0 5 49 1 0 0 0 0 7 51 1 0 0 0 0 9 10 1 0 0 0 0 9 22 2 0 0 0 0 10 28 1 0 0 0 0 11 14 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 30 1 0 0 0 0 13 50 1 0 0 0 0 14 51 1 0 0 0 0 15 23 1 0 0 0 0 15 48 1 0 0 0 0 16 29 1 0 0 0 0 16 52 1 0 0 0 0 18 54 1 0 0 0 0 19 24 1 0 0 0 0 19 67 1 0 0 0 0 20 68 1 0 0 0 0 21 1 1 1 0 0 0 21 32 1 0 0 0 0 21 69 1 0 0 0 0 22 23 1 0 0 0 0 22 52 1 0 0 0 0 23 53 1 1 0 0 0 24 33 1 0 0 0 0 24 55 1 6 0 0 0 25 18 1 1 0 0 0 25 34 1 0 0 0 0 25 70 1 0 0 0 0 26 20 1 1 0 0 0 26 35 1 0 0 0 0 26 71 1 0 0 0 0 27 49 1 0 0 0 0 27 50 1 6 0 0 0 28 50 1 6 0 0 0 28 51 1 0 0 0 0 29 53 1 1 0 0 0 29 56 1 0 0 0 0 30 49 1 0 0 0 0 30 72 1 6 0 0 0 31 17 1 1 0 0 0 31 48 1 0 0 0 0 31 73 1 0 0 0 0 32 37 1 0 0 0 0 32 57 1 1 0 0 0 33 39 1 0 0 0 0 33 58 1 1 0 0 0 34 36 1 0 0 0 0 34 59 1 6 0 0 0 35 38 1 0 0 0 0 35 60 1 6 0 0 0 36 40 1 0 0 0 0 36 61 1 1 0 0 0 37 41 1 0 0 0 0 37 62 1 1 0 0 0 38 42 1 0 0 0 0 38 63 1 1 0 0 0 39 43 1 0 0 0 0 39 64 1 6 0 0 0 40 44 1 0 0 0 0 40 65 1 6 0 0 0 41 45 1 0 0 0 0 41 74 1 6 0 0 0 42 46 1 0 0 0 0 42 75 1 6 0 0 0 43 67 1 0 0 0 0 43 74 1 1 0 0 0 44 70 1 0 0 0 0 44 75 1 1 0 0 0 45 68 1 1 0 0 0 45 69 1 0 0 0 0 46 71 1 0 0 0 0 46 72 1 1 0 0 0 47 53 1 0 0 0 0 47 66 2 0 0 0 0 47 73 1 0 0 0 0 50 6 1 6 0 0 0 51 52 1 1 0 0 0 52 8 1 1 0 0 0 53 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	341.16
Volume:	350.589
LogP:	2.516
LogD:	2.977
LogS:	-2.009
# Rotatable Bonds:	3
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.93
Synthetic Accessibility Score:	2.93
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.027
MDCK Permeability:	2.326676076336298e-05
Pgp-inhibitor:	0.476
Pgp-substrate:	0.927
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.241

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995
Plasma Protein Binding (PPB):	90.1384506225586%
Volume Distribution (VD):	1.254
Pgp-substrate:	10.370529174804688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.439
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.281
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.62
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	13.118
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.303
AMES Toxicity:	0.314
Rat Oral Acute Toxicity:	0.585
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.33
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC207738

Natural Product ID:	NPC207738
*Common Name:**	Porsapogenin 5
IUPAC Name:	n.a.
Synonyms:	Porsapogenin 5
Standard InCHIKey:	DYJFZMKQOTZRIY-UXVYOMMZSA-N
Standard InCHI:	InChI=1S/C53H84O22/c1-21-32(57)37(62)41(74-43-39(64)33(58)24(55)19-67-43)45(69-21)68-20-26-35(60)38(63)42(75-44-40(65)36(61)34(59)25(18-54)70-44)46(71-26)72-30-12-13-50(6)27(49(30,4)5)11-14-51(7)28(50)10-9-22-23-15-48(2,3)31-17-53(23,47(66)73-31)29(56)16-52(22,51)8/h9,21,23-46,54-65H,10-20H2,1-8H3/t21-,23+,24-,25-,26-,27+,28-,29-,30+,31+,32+,33+,34-,35-,36+,37+,38+,39-,40-,41-,42-,43+,44+,45-,46+,50+,51-,52-,53-/m1/s1
SMILES:	C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)[C@@H]6C[C@@]5([C@@H](C[C@@]43C)O)C(=O)O6)C2(C)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)O1)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525986
PubChem CID:	44566620
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12181	Albizia julibrissin	Species	Fabaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[559035]

☑ 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 NPC207738 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	259
0.1-0.2	1678
0.2-0.3	5316
0.3-0.4	11398
0.4-0.5	9940
0.5-0.6	6306
0.6-0.7	4273
0.7-0.8	2053
0.8-0.85	648
0.85-0.9	369
0.9-0.95	391
0.95-1	66

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC105800
0.9908	High Similarity	NPC232237
0.9817	High Similarity	NPC475119
0.9817	High Similarity	NPC473824
0.973	High Similarity	NPC267694
0.973	High Similarity	NPC142151
0.973	High Similarity	NPC473645
0.973	High Similarity	NPC110385
0.973	High Similarity	NPC144644
0.973	High Similarity	NPC37860
0.973	High Similarity	NPC153673
0.9725	High Similarity	NPC305267
0.9725	High Similarity	NPC37134
0.9725	High Similarity	NPC26626
0.9725	High Similarity	NPC476992
0.9725	High Similarity	NPC291903
0.9725	High Similarity	NPC75287
0.9725	High Similarity	NPC288205
0.9725	High Similarity	NPC51465
0.9643	High Similarity	NPC275225
0.9643	High Similarity	NPC293031
0.9643	High Similarity	NPC51099
0.9643	High Similarity	NPC68767
0.9636	High Similarity	NPC309223
0.9636	High Similarity	NPC102505
0.9636	High Similarity	NPC470876
0.9636	High Similarity	NPC33012
0.9636	High Similarity	NPC85154
0.9636	High Similarity	NPC475209
0.9636	High Similarity	NPC300419
0.9636	High Similarity	NPC104137
0.9636	High Similarity	NPC69811
0.9636	High Similarity	NPC191827
0.9636	High Similarity	NPC220160
0.9636	High Similarity	NPC123522
0.9636	High Similarity	NPC473452
0.9636	High Similarity	NPC8524
0.9636	High Similarity	NPC475514
0.9636	High Similarity	NPC286457
0.9633	High Similarity	NPC164389
0.9633	High Similarity	NPC475486
0.955	High Similarity	NPC475899
0.955	High Similarity	NPC237191
0.955	High Similarity	NPC473459
0.9545	High Similarity	NPC471384
0.9545	High Similarity	NPC161674
0.9541	High Similarity	NPC133818
0.9541	High Similarity	NPC192600
0.9541	High Similarity	NPC174720
0.9541	High Similarity	NPC241909
0.9541	High Similarity	NPC155410
0.9541	High Similarity	NPC166422
0.9541	High Similarity	NPC295823
0.9541	High Similarity	NPC323341
0.9541	High Similarity	NPC473826
0.9541	High Similarity	NPC114304
0.9541	High Similarity	NPC46665
0.9541	High Similarity	NPC309714
0.9541	High Similarity	NPC475467
0.9541	High Similarity	NPC219180
0.9541	High Similarity	NPC475287
0.9541	High Similarity	NPC251263
0.9541	High Similarity	NPC114287
0.9541	High Similarity	NPC151543
0.9478	High Similarity	NPC470218
0.9474	High Similarity	NPC235405
0.9474	High Similarity	NPC30735
0.9474	High Similarity	NPC281148
0.9464	High Similarity	NPC51564
0.9464	High Similarity	NPC477464
0.9464	High Similarity	NPC471577
0.9464	High Similarity	NPC135849
0.9464	High Similarity	NPC25663
0.9464	High Similarity	NPC473386
0.9459	High Similarity	NPC136768
0.9459	High Similarity	NPC471580
0.9459	High Similarity	NPC68175
0.9459	High Similarity	NPC148417
0.9459	High Similarity	NPC110633
0.9459	High Similarity	NPC323359
0.9455	High Similarity	NPC224381
0.9455	High Similarity	NPC305981
0.9455	High Similarity	NPC4328
0.9455	High Similarity	NPC236638
0.9455	High Similarity	NPC309907
0.9455	High Similarity	NPC469782
0.9455	High Similarity	NPC227551
0.9455	High Similarity	NPC471550
0.9455	High Similarity	NPC161717
0.9455	High Similarity	NPC119592
0.9455	High Similarity	NPC76972
0.9455	High Similarity	NPC476068
0.9455	High Similarity	NPC43550
0.9455	High Similarity	NPC250247
0.9455	High Similarity	NPC60557
0.9455	High Similarity	NPC67857
0.9455	High Similarity	NPC41061
0.9455	High Similarity	NPC79643
0.9455	High Similarity	NPC123199
0.9455	High Similarity	NPC71065
0.9455	High Similarity	NPC473714
0.9455	High Similarity	NPC475160
0.9455	High Similarity	NPC57484
0.9455	High Similarity	NPC294453
0.9455	High Similarity	NPC293330
0.9455	High Similarity	NPC54636
0.9455	High Similarity	NPC70809
0.9455	High Similarity	NPC471385
0.9455	High Similarity	NPC204414
0.9455	High Similarity	NPC475140
0.9455	High Similarity	NPC261506
0.9455	High Similarity	NPC298034
0.9455	High Similarity	NPC202828
0.9455	High Similarity	NPC100639
0.9455	High Similarity	NPC65105
0.945	High Similarity	NPC101744
0.945	High Similarity	NPC469946
0.945	High Similarity	NPC104071
0.945	High Similarity	NPC1046
0.945	High Similarity	NPC104400
0.945	High Similarity	NPC471383
0.945	High Similarity	NPC79718
0.945	High Similarity	NPC475516
0.945	High Similarity	NPC473373
0.945	High Similarity	NPC292677
0.945	High Similarity	NPC276093
0.945	High Similarity	NPC10320
0.945	High Similarity	NPC80843
0.945	High Similarity	NPC139044
0.945	High Similarity	NPC109079
0.945	High Similarity	NPC475504
0.945	High Similarity	NPC102439
0.945	High Similarity	NPC324875
0.945	High Similarity	NPC257468
0.9391	High Similarity	NPC470477
0.9386	High Similarity	NPC107966
0.9386	High Similarity	NPC40775
0.9386	High Similarity	NPC475591
0.9386	High Similarity	NPC235438
0.9386	High Similarity	NPC21691
0.9386	High Similarity	NPC249848
0.9386	High Similarity	NPC4749
0.9386	High Similarity	NPC80986
0.9386	High Similarity	NPC187290
0.9386	High Similarity	NPC10607
0.9386	High Similarity	NPC236870
0.9381	High Similarity	NPC476991
0.9375	High Similarity	NPC470514
0.9375	High Similarity	NPC36831
0.9375	High Similarity	NPC470513
0.9369	High Similarity	NPC160415
0.9369	High Similarity	NPC58448
0.9364	High Similarity	NPC475208
0.9364	High Similarity	NPC96641
0.9364	High Similarity	NPC73318
0.9364	High Similarity	NPC473343
0.9364	High Similarity	NPC238935
0.9364	High Similarity	NPC258885
0.9364	High Similarity	NPC150400
0.9364	High Similarity	NPC134835
0.9364	High Similarity	NPC163183
0.9364	High Similarity	NPC124296
0.9358	High Similarity	NPC31839
0.9358	High Similarity	NPC164419
0.9304	High Similarity	NPC302543
0.9304	High Similarity	NPC283417
0.9304	High Similarity	NPC200049
0.9304	High Similarity	NPC258617
0.9304	High Similarity	NPC257211
0.9298	High Similarity	NPC114484
0.9298	High Similarity	NPC187618
0.9298	High Similarity	NPC86222
0.9298	High Similarity	NPC302887
0.9298	High Similarity	NPC222580
0.9298	High Similarity	NPC301449
0.9298	High Similarity	NPC297263
0.9298	High Similarity	NPC64715
0.9298	High Similarity	NPC171544
0.9298	High Similarity	NPC11242
0.9298	High Similarity	NPC31838
0.9298	High Similarity	NPC104372
0.9298	High Similarity	NPC477463
0.9298	High Similarity	NPC22956
0.9298	High Similarity	NPC223301
0.9298	High Similarity	NPC62725
0.9298	High Similarity	NPC159309
0.9286	High Similarity	NPC185466
0.9273	High Similarity	NPC473383
0.9273	High Similarity	NPC256798
0.9273	High Similarity	NPC128925
0.9273	High Similarity	NPC139894
0.9273	High Similarity	NPC48249
0.9266	High Similarity	NPC127056
0.9266	High Similarity	NPC475296
0.9266	High Similarity	NPC270667
0.9266	High Similarity	NPC279554
0.9266	High Similarity	NPC474589
0.9266	High Similarity	NPC174679
0.9266	High Similarity	NPC242611
0.9266	High Similarity	NPC90856

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 NPC207738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1958
0.2-0.3	4027
0.3-0.4	1909
0.4-0.5	539
0.5-0.6	294
0.6-0.7	155
0.7-0.8	27
0.8-0.85	14
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8974	High Similarity	NPD8328	Phase 3
0.8783	High Similarity	NPD8295	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8362	Intermediate Similarity	NPD8133	Approved
0.8182	Intermediate Similarity	NPD8517	Approved
0.8182	Intermediate Similarity	NPD8515	Approved
0.8182	Intermediate Similarity	NPD8516	Approved
0.8033	Intermediate Similarity	NPD8513	Phase 3
0.7845	Intermediate Similarity	NPD6412	Phase 2
0.7805	Intermediate Similarity	NPD8294	Approved
0.7805	Intermediate Similarity	NPD8377	Approved
0.7795	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD6686	Approved
0.7742	Intermediate Similarity	NPD8378	Approved
0.7742	Intermediate Similarity	NPD8296	Approved
0.7742	Intermediate Similarity	NPD8380	Approved
0.7742	Intermediate Similarity	NPD8335	Approved
0.7742	Intermediate Similarity	NPD8379	Approved
0.7734	Intermediate Similarity	NPD7319	Approved
0.7638	Intermediate Similarity	NPD7507	Approved
0.7611	Intermediate Similarity	NPD7902	Approved
0.76	Intermediate Similarity	NPD8033	Approved
0.7578	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD7748	Approved
0.7438	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD6370	Approved
0.7373	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7328	Approved
0.736	Intermediate Similarity	NPD7327	Approved
0.7345	Intermediate Similarity	NPD7900	Approved
0.7345	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7515	Phase 2
0.7302	Intermediate Similarity	NPD7516	Approved
0.7287	Intermediate Similarity	NPD7492	Approved
0.7244	Intermediate Similarity	NPD6059	Approved
0.7244	Intermediate Similarity	NPD6054	Approved
0.7231	Intermediate Similarity	NPD6616	Approved
0.7188	Intermediate Similarity	NPD7503	Approved
0.7176	Intermediate Similarity	NPD7078	Approved
0.7168	Intermediate Similarity	NPD8034	Phase 2
0.7168	Intermediate Similarity	NPD8035	Phase 2
0.7109	Intermediate Similarity	NPD6319	Approved
0.7054	Intermediate Similarity	NPD6015	Approved
0.7054	Intermediate Similarity	NPD6016	Approved
0.7049	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8074	Phase 3
0.7008	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD5988	Approved
0.696	Remote Similarity	NPD6882	Approved
0.696	Remote Similarity	NPD8297	Approved
0.6957	Remote Similarity	NPD6399	Phase 3
0.6957	Remote Similarity	NPD8171	Discontinued
0.6949	Remote Similarity	NPD4225	Approved
0.6949	Remote Similarity	NPD7638	Approved
0.6947	Remote Similarity	NPD6067	Discontinued
0.6891	Remote Similarity	NPD7639	Approved
0.6891	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD6009	Approved
0.6855	Remote Similarity	NPD6372	Approved
0.6855	Remote Similarity	NPD6373	Approved
0.6855	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4632	Approved
0.6748	Remote Similarity	NPD6675	Approved
0.6748	Remote Similarity	NPD7128	Approved
0.6748	Remote Similarity	NPD6402	Approved
0.6748	Remote Similarity	NPD5739	Approved
0.6746	Remote Similarity	NPD6649	Approved
0.6746	Remote Similarity	NPD6650	Approved
0.6741	Remote Similarity	NPD6033	Approved
0.6739	Remote Similarity	NPD8450	Suspended
0.6724	Remote Similarity	NPD6411	Approved
0.6697	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD8449	Approved
0.664	Remote Similarity	NPD6899	Approved
0.664	Remote Similarity	NPD6881	Approved
0.664	Remote Similarity	NPD7320	Approved
0.6614	Remote Similarity	NPD8130	Phase 1
0.6613	Remote Similarity	NPD6008	Approved
0.6579	Remote Similarity	NPD3618	Phase 1
0.656	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5701	Approved
0.656	Remote Similarity	NPD5697	Approved
0.6552	Remote Similarity	NPD6101	Approved
0.6552	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6921	Approved
0.6535	Remote Similarity	NPD7102	Approved
0.6535	Remote Similarity	NPD6883	Approved
0.6535	Remote Similarity	NPD4634	Approved
0.6535	Remote Similarity	NPD7290	Approved
0.6484	Remote Similarity	NPD6617	Approved
0.6484	Remote Similarity	NPD6847	Approved
0.6484	Remote Similarity	NPD6869	Approved
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6013	Approved
0.6457	Remote Similarity	NPD6014	Approved
0.6457	Remote Similarity	NPD6012	Approved
0.6446	Remote Similarity	NPD6084	Phase 2
0.6446	Remote Similarity	NPD6083	Phase 2
0.6444	Remote Similarity	NPD7604	Phase 2
0.6441	Remote Similarity	NPD7983	Approved
0.6418	Remote Similarity	NPD5983	Phase 2
0.641	Remote Similarity	NPD5328	Approved
0.6404	Remote Similarity	NPD4786	Approved
0.6387	Remote Similarity	NPD5779	Approved
0.6387	Remote Similarity	NPD5778	Approved
0.6378	Remote Similarity	NPD6011	Approved
0.6377	Remote Similarity	NPD8337	Approved
0.6377	Remote Similarity	NPD8336	Approved
0.6372	Remote Similarity	NPD3667	Approved
0.6371	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6698	Approved
0.6356	Remote Similarity	NPD46	Approved
0.635	Remote Similarity	NPD6336	Discontinued
0.6316	Remote Similarity	NPD3669	Approved
0.6316	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4755	Approved
0.6304	Remote Similarity	NPD8448	Approved
0.6303	Remote Similarity	NPD6079	Approved
0.6299	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7146	Approved
0.6293	Remote Similarity	NPD6409	Approved
0.6293	Remote Similarity	NPD7334	Approved
0.6293	Remote Similarity	NPD6684	Approved
0.6293	Remote Similarity	NPD5330	Approved
0.6293	Remote Similarity	NPD7521	Approved
0.6288	Remote Similarity	NPD6940	Discontinued
0.6286	Remote Similarity	NPD5956	Approved
0.6286	Remote Similarity	NPD8391	Approved
0.6286	Remote Similarity	NPD8390	Approved
0.6286	Remote Similarity	NPD8392	Approved
0.6281	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD8341	Approved
0.6277	Remote Similarity	NPD8342	Approved
0.6277	Remote Similarity	NPD8340	Approved
0.6277	Remote Similarity	NPD8299	Approved
0.626	Remote Similarity	NPD5696	Approved
0.626	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4202	Approved
0.6239	Remote Similarity	NPD3573	Approved
0.6232	Remote Similarity	NPD8451	Approved
0.623	Remote Similarity	NPD4697	Phase 3
0.621	Remote Similarity	NPD4696	Approved
0.621	Remote Similarity	NPD5286	Approved
0.621	Remote Similarity	NPD5285	Approved
0.621	Remote Similarity	NPD4700	Approved
0.62	Remote Similarity	NPD7625	Phase 1
0.6198	Remote Similarity	NPD5282	Discontinued
0.6197	Remote Similarity	NPD8338	Approved
0.6195	Remote Similarity	NPD7525	Registered
0.6186	Remote Similarity	NPD5737	Approved
0.6186	Remote Similarity	NPD6903	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6176	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7637	Suspended
0.6165	Remote Similarity	NPD6274	Approved
0.6161	Remote Similarity	NPD6697	Approved
0.6161	Remote Similarity	NPD6114	Approved
0.6161	Remote Similarity	NPD6115	Approved
0.6161	Remote Similarity	NPD6118	Approved
0.6154	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6371	Approved
0.6148	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD5695	Phase 3
0.6148	Remote Similarity	NPD7101	Approved
0.614	Remote Similarity	NPD1780	Approved
0.614	Remote Similarity	NPD1779	Approved
0.6134	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8080	Discontinued
0.6121	Remote Similarity	NPD3665	Phase 1
0.6121	Remote Similarity	NPD3133	Approved
0.6121	Remote Similarity	NPD3666	Approved
0.6111	Remote Similarity	NPD5224	Approved
0.6111	Remote Similarity	NPD5211	Phase 2
0.6111	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD4633	Approved
0.6111	Remote Similarity	NPD5226	Approved
0.6098	Remote Similarity	NPD5222	Approved
0.6098	Remote Similarity	NPD7839	Suspended
0.6098	Remote Similarity	NPD5221	Approved
0.6098	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD4767	Approved
0.6094	Remote Similarity	NPD4768	Approved
0.6087	Remote Similarity	NPD7829	Approved
0.6087	Remote Similarity	NPD7830	Approved
0.6074	Remote Similarity	NPD6335	Approved
0.6071	Remote Similarity	NPD6116	Phase 1
0.6063	Remote Similarity	NPD5174	Approved
0.6063	Remote Similarity	NPD5175	Approved
0.6058	Remote Similarity	NPD8444	Approved
0.6058	Remote Similarity	NPD6909	Approved
0.6058	Remote Similarity	NPD6908	Approved
0.6058	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD5173	Approved
0.6045	Remote Similarity	NPD6868	Approved
0.6032	Remote Similarity	NPD5223	Approved
0.6027	Remote Similarity	NPD7966	Clinical (unspecified phase)

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