NPASS Compound

Structure

CID43252 OpenBabel06191715372D 48 54 0 0 1 0 0 0 0 0999 V2000 -2.5206 4.4313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4692 3.7923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 5.3957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6973 3.9240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5503 3.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6832 2.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7845 1.9557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2500 4.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8493 -0.4903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4007 3.9221 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4886 3.7920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8510 4.4145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6976 2.9433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6983 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0984 3.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6998 0.9807 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3999 2.9420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5497 1.4710 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8502 1.4715 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2483 2.4511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6995 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2480 1.4705 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6980 0.9817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8505 2.4521 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8496 -0.4908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7004 2.9424 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8487 1.4720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6063 3.4292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5500 2.4516 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0976 2.9405 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9812 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0295 2.6368 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 -0.0019 4.6410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0011 3.9241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 2.4532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5703 -0.5036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9589 0.7592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8493 -1.4942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6231 3.4283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8172 1.6424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0014 2.9426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 3.9236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8485 2.4527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5479 0.4913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0309 4.2227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 33 1 0 0 0 0 9 11 1 0 0 0 0 9 16 2 0 0 0 0 10 34 1 0 0 0 0 11 1 1 1 0 0 0 11 18 1 0 0 0 0 12 35 2 0 0 0 0 12 44 1 0 0 0 0 13 36 2 0 0 0 0 13 45 1 0 0 0 0 14 37 2 0 0 0 0 14 46 1 0 0 0 0 15 10 1 1 0 0 0 15 24 1 0 0 0 0 15 47 1 0 0 0 0 16 31 1 0 0 0 0 16 48 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 19 30 1 0 0 0 0 20 25 1 0 0 0 0 20 32 1 0 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 38 1 0 0 0 0 23 39 1 0 0 0 0 24 28 1 0 0 0 0 24 47 1 0 0 0 0 25 27 1 0 0 0 0 25 44 1 0 0 0 0 26 34 1 0 0 0 0 26 40 2 0 0 0 0 27 30 1 0 0 0 0 27 45 1 0 0 0 0 28 32 1 0 0 0 0 28 46 1 0 0 0 0 29 33 1 0 0 0 0 29 41 2 0 0 0 0 29 48 1 0 0 0 0 31 33 1 0 0 0 0 32 34 1 0 0 0 0 33 42 1 0 0 0 0 34 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	676.27
Volume:	643.969
LogP:	1.518
LogD:	1.28
LogS:	-2.589
# Rotatable Bonds:	6
TPSA:	215.72
# H-Bond Aceptor:	14
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	6.407
Fsp3:	0.794
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:	-5.425
MDCK Permeability:	0.00033373426413163543
Pgp-inhibitor:	0.996
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.696
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	27.487781524658203%
Volume Distribution (VD):	0.558
Pgp-substrate:	44.08799743652344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.328
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	1.792
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.775
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.376
Maximum Recommended Daily Dose:	0.087
Skin Sensitization:	0.144
Carcinogencity:	0.23
Eye Corrosion:	0.099
Eye Irritation:	0.014
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC43252

Natural Product ID:	NPC43252
*Common Name:**	Taccalonolide Ab
IUPAC Name:	n.a.
Synonyms:	Taccalonolide AB
Standard InCHIKey:	RBNQHZWCHFIXOW-UUXMOSEOSA-N
Standard InCHI:	InChI=1S/C34H44O14/c1-11-9-16-31(6,33(8,42)29(41)48-16)21-18(11)30(5)19(23(21)39)17-20(25(44-12(2)35)27(30)45-13(3)36)32(7)28(46-14(4)37)24-15(47-24)10-34(32,43)26(40)22(17)38/h9,11,15,17-25,27-28,38-39,42-43H,10H2,1-8H3/t11-,15+,17+,18+,19-,20-,21+,22-,23-,24+,25+,27+,28+,30-,31+,32+,33-,34+/m1/s1
SMILES:	C[C@@H]1C=C2[C@@](C)([C@H]3[C@H]1[C@]1(C)[C@H]([C@H]4[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)[C@@]1(C)[C@H]([C@@H]5[C@H](C[C@@]1(C(=O)[C@@H]4O)O)O5)OC(=O)C)[C@H]3O)[C@@](C)(C(=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821846
PubChem CID:	53474203
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	rhizomes	SiMao City, Yunnan Province, China	1996-OCT	PMID[11908966]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[12350150]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20715765]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33253561]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13332	Tacca chantrieri	Species	Taccaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2767.0	nM	PMID[547533]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2767.0	nM	PMID[547534]

☑ 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 NPC43252 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	305
0.1-0.2	1897
0.2-0.3	5615
0.3-0.4	10365
0.4-0.5	11007
0.5-0.6	6250
0.6-0.7	5368
0.7-0.8	1777
0.8-0.85	96
0.85-0.9	12
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135038
0.9912	High Similarity	NPC65858
0.9825	High Similarity	NPC267822
0.9739	High Similarity	NPC169818
0.8783	High Similarity	NPC280782
0.875	High Similarity	NPC222688
0.8455	Intermediate Similarity	NPC473255
0.8435	Intermediate Similarity	NPC94529
0.843	Intermediate Similarity	NPC471406
0.8417	Intermediate Similarity	NPC324253
0.8403	Intermediate Similarity	NPC40632
0.8403	Intermediate Similarity	NPC328374
0.8403	Intermediate Similarity	NPC96312
0.8403	Intermediate Similarity	NPC251236
0.839	Intermediate Similarity	NPC49451
0.8361	Intermediate Similarity	NPC102822
0.8361	Intermediate Similarity	NPC477046
0.8348	Intermediate Similarity	NPC59530
0.8346	Intermediate Similarity	NPC473805
0.8346	Intermediate Similarity	NPC473519
0.8333	Intermediate Similarity	NPC470854
0.8333	Intermediate Similarity	NPC474654
0.8333	Intermediate Similarity	NPC97908
0.8333	Intermediate Similarity	NPC231529
0.8333	Intermediate Similarity	NPC287343
0.8333	Intermediate Similarity	NPC122033
0.8333	Intermediate Similarity	NPC470880
0.832	Intermediate Similarity	NPC470882
0.832	Intermediate Similarity	NPC473253
0.8319	Intermediate Similarity	NPC473798
0.8305	Intermediate Similarity	NPC90769
0.8281	Intermediate Similarity	NPC102015
0.8279	Intermediate Similarity	NPC109973
0.8261	Intermediate Similarity	NPC231530
0.8261	Intermediate Similarity	NPC196528
0.8261	Intermediate Similarity	NPC278628
0.825	Intermediate Similarity	NPC49492
0.825	Intermediate Similarity	NPC179626
0.825	Intermediate Similarity	NPC474734
0.825	Intermediate Similarity	NPC266728
0.8235	Intermediate Similarity	NPC202889
0.8235	Intermediate Similarity	NPC97002
0.8235	Intermediate Similarity	NPC194100
0.8197	Intermediate Similarity	NPC470777
0.8197	Intermediate Similarity	NPC473203
0.8182	Intermediate Similarity	NPC176513
0.8182	Intermediate Similarity	NPC470775
0.8182	Intermediate Similarity	NPC473590
0.8175	Intermediate Similarity	NPC473265
0.8174	Intermediate Similarity	NPC29705
0.8174	Intermediate Similarity	NPC471293
0.816	Intermediate Similarity	NPC475194
0.816	Intermediate Similarity	NPC469790
0.8151	Intermediate Similarity	NPC474516
0.813	Intermediate Similarity	NPC251226
0.8125	Intermediate Similarity	NPC473838
0.8125	Intermediate Similarity	NPC475389
0.812	Intermediate Similarity	NPC258323
0.8115	Intermediate Similarity	NPC17772
0.8115	Intermediate Similarity	NPC204552
0.8115	Intermediate Similarity	NPC118638
0.8115	Intermediate Similarity	NPC188667
0.811	Intermediate Similarity	NPC69273
0.811	Intermediate Similarity	NPC293623
0.811	Intermediate Similarity	NPC168899
0.8103	Intermediate Similarity	NPC475571
0.8099	Intermediate Similarity	NPC235539
0.8099	Intermediate Similarity	NPC134869
0.8099	Intermediate Similarity	NPC16081
0.8099	Intermediate Similarity	NPC173686
0.8099	Intermediate Similarity	NPC270958
0.8099	Intermediate Similarity	NPC207217
0.8099	Intermediate Similarity	NPC152199
0.8095	Intermediate Similarity	NPC174367
0.8095	Intermediate Similarity	NPC473635
0.8095	Intermediate Similarity	NPC47113
0.8087	Intermediate Similarity	NPC191892
0.8087	Intermediate Similarity	NPC140723
0.8083	Intermediate Similarity	NPC7921
0.8083	Intermediate Similarity	NPC477266
0.8083	Intermediate Similarity	NPC250109
0.8083	Intermediate Similarity	NPC52634
0.8083	Intermediate Similarity	NPC962
0.8083	Intermediate Similarity	NPC198539
0.8083	Intermediate Similarity	NPC73300
0.8083	Intermediate Similarity	NPC208998
0.8083	Intermediate Similarity	NPC317210
0.8083	Intermediate Similarity	NPC108721
0.808	Intermediate Similarity	NPC473979
0.808	Intermediate Similarity	NPC227397
0.8067	Intermediate Similarity	NPC472003
0.8067	Intermediate Similarity	NPC43775
0.8065	Intermediate Similarity	NPC159456
0.8065	Intermediate Similarity	NPC310511
0.8065	Intermediate Similarity	NPC4021
0.8062	Intermediate Similarity	NPC471855
0.8051	Intermediate Similarity	NPC27814
0.8049	Intermediate Similarity	NPC42673
0.8049	Intermediate Similarity	NPC475041
0.8049	Intermediate Similarity	NPC469488
0.8034	Intermediate Similarity	NPC144854
0.8034	Intermediate Similarity	NPC165873
0.8034	Intermediate Similarity	NPC3316
0.8033	Intermediate Similarity	NPC471854
0.8031	Intermediate Similarity	NPC305496
0.8017	Intermediate Similarity	NPC326542
0.8017	Intermediate Similarity	NPC323821
0.8017	Intermediate Similarity	NPC143268
0.8017	Intermediate Similarity	NPC45218
0.8017	Intermediate Similarity	NPC18547
0.8017	Intermediate Similarity	NPC268238
0.8017	Intermediate Similarity	NPC474906
0.8015	Intermediate Similarity	NPC256618
0.8015	Intermediate Similarity	NPC219058
0.8	Intermediate Similarity	NPC71348
0.8	Intermediate Similarity	NPC289312
0.8	Intermediate Similarity	NPC477054
0.8	Intermediate Similarity	NPC472002
0.8	Intermediate Similarity	NPC207251
0.8	Intermediate Similarity	NPC473928
0.8	Intermediate Similarity	NPC11252
0.8	Intermediate Similarity	NPC269642
0.7984	Intermediate Similarity	NPC154491
0.7984	Intermediate Similarity	NPC268530
0.7984	Intermediate Similarity	NPC241192
0.7984	Intermediate Similarity	NPC112038
0.7984	Intermediate Similarity	NPC241008
0.7983	Intermediate Similarity	NPC5284
0.797	Intermediate Similarity	NPC290746
0.797	Intermediate Similarity	NPC79250
0.7969	Intermediate Similarity	NPC476091
0.7969	Intermediate Similarity	NPC476078
0.7967	Intermediate Similarity	NPC311554
0.7967	Intermediate Similarity	NPC470776
0.7967	Intermediate Similarity	NPC257457
0.7967	Intermediate Similarity	NPC297179
0.7967	Intermediate Similarity	NPC251310
0.7966	Intermediate Similarity	NPC293850
0.7966	Intermediate Similarity	NPC154608
0.7966	Intermediate Similarity	NPC277017
0.7966	Intermediate Similarity	NPC192813
0.7953	Intermediate Similarity	NPC293112
0.7951	Intermediate Similarity	NPC259306
0.7951	Intermediate Similarity	NPC298278
0.7951	Intermediate Similarity	NPC474046
0.7951	Intermediate Similarity	NPC470628
0.7949	Intermediate Similarity	NPC477877
0.7949	Intermediate Similarity	NPC472655
0.7949	Intermediate Similarity	NPC470587
0.7939	Intermediate Similarity	NPC475376
0.7937	Intermediate Similarity	NPC91693
0.7937	Intermediate Similarity	NPC11895
0.7937	Intermediate Similarity	NPC265557
0.7937	Intermediate Similarity	NPC18945
0.7937	Intermediate Similarity	NPC105926
0.7923	Intermediate Similarity	NPC42206
0.792	Intermediate Similarity	NPC275675
0.792	Intermediate Similarity	NPC470921
0.7917	Intermediate Similarity	NPC201992
0.7917	Intermediate Similarity	NPC171888
0.7917	Intermediate Similarity	NPC146945
0.7913	Intermediate Similarity	NPC477051
0.7913	Intermediate Similarity	NPC155974
0.7913	Intermediate Similarity	NPC477052
0.7913	Intermediate Similarity	NPC477053
0.7907	Intermediate Similarity	NPC221414
0.7907	Intermediate Similarity	NPC54614
0.7907	Intermediate Similarity	NPC309096
0.7907	Intermediate Similarity	NPC471407
0.7903	Intermediate Similarity	NPC477071
0.7903	Intermediate Similarity	NPC161065
0.7903	Intermediate Similarity	NPC230513
0.7903	Intermediate Similarity	NPC61520
0.7903	Intermediate Similarity	NPC161738
0.7899	Intermediate Similarity	NPC141350
0.7899	Intermediate Similarity	NPC304495
0.7899	Intermediate Similarity	NPC310546
0.7874	Intermediate Similarity	NPC476729
0.7874	Intermediate Similarity	NPC81736
0.7874	Intermediate Similarity	NPC172154
0.7874	Intermediate Similarity	NPC24651
0.7874	Intermediate Similarity	NPC8369
0.7869	Intermediate Similarity	NPC243354
0.7869	Intermediate Similarity	NPC247069
0.7869	Intermediate Similarity	NPC117712
0.7869	Intermediate Similarity	NPC469877
0.7869	Intermediate Similarity	NPC470919
0.7863	Intermediate Similarity	NPC475036
0.7863	Intermediate Similarity	NPC301787
0.7863	Intermediate Similarity	NPC65523
0.7863	Intermediate Similarity	NPC328737
0.7863	Intermediate Similarity	NPC47281
0.7857	Intermediate Similarity	NPC28532
0.7857	Intermediate Similarity	NPC312833
0.7857	Intermediate Similarity	NPC170538
0.7857	Intermediate Similarity	NPC475431
0.7851	Intermediate Similarity	NPC302146
0.7851	Intermediate Similarity	NPC234042
0.7851	Intermediate Similarity	NPC152117
0.7851	Intermediate Similarity	NPC477489

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 NPC43252 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	2178
0.2-0.3	4040
0.3-0.4	1702
0.4-0.5	510
0.5-0.6	242
0.6-0.7	148
0.7-0.8	63
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD8297	Approved
0.7969	Intermediate Similarity	NPD7736	Approved
0.7949	Intermediate Similarity	NPD6008	Approved
0.7899	Intermediate Similarity	NPD6373	Approved
0.7899	Intermediate Similarity	NPD6372	Approved
0.784	Intermediate Similarity	NPD6319	Approved
0.7815	Intermediate Similarity	NPD7320	Approved
0.7797	Intermediate Similarity	NPD5739	Approved
0.7797	Intermediate Similarity	NPD6675	Approved
0.7797	Intermediate Similarity	NPD7128	Approved
0.7797	Intermediate Similarity	NPD6402	Approved
0.7787	Intermediate Similarity	NPD4632	Approved
0.7769	Intermediate Similarity	NPD6650	Approved
0.7769	Intermediate Similarity	NPD6649	Approved
0.7752	Intermediate Similarity	NPD8293	Discontinued
0.7734	Intermediate Similarity	NPD7492	Approved
0.7698	Intermediate Similarity	NPD6059	Approved
0.7698	Intermediate Similarity	NPD6054	Approved
0.7674	Intermediate Similarity	NPD6616	Approved
0.7667	Intermediate Similarity	NPD6881	Approved
0.7667	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6899	Approved
0.7623	Intermediate Similarity	NPD8130	Phase 1
0.7615	Intermediate Similarity	NPD7078	Approved
0.7583	Intermediate Similarity	NPD5697	Approved
0.7583	Intermediate Similarity	NPD5701	Approved
0.7578	Intermediate Similarity	NPD6370	Approved
0.7561	Intermediate Similarity	NPD6882	Approved
0.7541	Intermediate Similarity	NPD7102	Approved
0.7541	Intermediate Similarity	NPD7290	Approved
0.7541	Intermediate Similarity	NPD6883	Approved
0.7538	Intermediate Similarity	NPD7507	Approved
0.7519	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD6847	Approved
0.748	Intermediate Similarity	NPD6617	Approved
0.748	Intermediate Similarity	NPD6869	Approved
0.746	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6009	Approved
0.7459	Intermediate Similarity	NPD6014	Approved
0.7459	Intermediate Similarity	NPD6013	Approved
0.7459	Intermediate Similarity	NPD6012	Approved
0.7442	Intermediate Similarity	NPD5988	Approved
0.7385	Intermediate Similarity	NPD8328	Phase 3
0.7377	Intermediate Similarity	NPD6011	Approved
0.7364	Intermediate Similarity	NPD5983	Phase 2
0.735	Intermediate Similarity	NPD4755	Approved
0.7344	Intermediate Similarity	NPD7516	Approved
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7115	Discovery
0.7317	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1700	Approved
0.7273	Intermediate Similarity	NPD6336	Discontinued
0.7266	Intermediate Similarity	NPD7328	Approved
0.7266	Intermediate Similarity	NPD7327	Approved
0.7258	Intermediate Similarity	NPD4634	Approved
0.7258	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4696	Approved
0.7227	Intermediate Similarity	NPD4700	Approved
0.7227	Intermediate Similarity	NPD5285	Approved
0.7227	Intermediate Similarity	NPD5286	Approved
0.7203	Intermediate Similarity	NPD6083	Phase 2
0.7203	Intermediate Similarity	NPD6084	Phase 2
0.7164	Intermediate Similarity	NPD6033	Approved
0.7155	Intermediate Similarity	NPD6399	Phase 3
0.7154	Intermediate Similarity	NPD6412	Phase 2
0.7131	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6274	Approved
0.7107	Intermediate Similarity	NPD5224	Approved
0.7107	Intermediate Similarity	NPD5225	Approved
0.7107	Intermediate Similarity	NPD5211	Phase 2
0.7107	Intermediate Similarity	NPD5226	Approved
0.7107	Intermediate Similarity	NPD4633	Approved
0.7099	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD8380	Approved
0.7099	Intermediate Similarity	NPD8296	Approved
0.7099	Intermediate Similarity	NPD8335	Approved
0.7099	Intermediate Similarity	NPD8379	Approved
0.7099	Intermediate Similarity	NPD8033	Approved
0.7099	Intermediate Similarity	NPD8378	Approved
0.7099	Intermediate Similarity	NPD6921	Approved
0.7077	Intermediate Similarity	NPD7101	Approved
0.7077	Intermediate Similarity	NPD7100	Approved
0.7073	Intermediate Similarity	NPD4768	Approved
0.7073	Intermediate Similarity	NPD4767	Approved
0.7049	Intermediate Similarity	NPD5174	Approved
0.7049	Intermediate Similarity	NPD5175	Approved
0.7034	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5223	Approved
0.7023	Intermediate Similarity	NPD8377	Approved
0.7023	Intermediate Similarity	NPD8294	Approved
0.7016	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6053	Discontinued
0.7	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD6335	Approved
0.6992	Remote Similarity	NPD5141	Approved
0.697	Remote Similarity	NPD6908	Approved
0.697	Remote Similarity	NPD6909	Approved
0.696	Remote Similarity	NPD4729	Approved
0.696	Remote Similarity	NPD4730	Approved
0.6953	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD6317	Approved
0.6923	Remote Similarity	NPD8034	Phase 2
0.6917	Remote Similarity	NPD7902	Approved
0.6911	Remote Similarity	NPD4754	Approved
0.6891	Remote Similarity	NPD5695	Phase 3
0.687	Remote Similarity	NPD6314	Approved
0.687	Remote Similarity	NPD6313	Approved
0.686	Remote Similarity	NPD7638	Approved
0.685	Remote Similarity	NPD5250	Approved
0.685	Remote Similarity	NPD5249	Phase 3
0.685	Remote Similarity	NPD5251	Approved
0.685	Remote Similarity	NPD5248	Approved
0.685	Remote Similarity	NPD5247	Approved
0.6842	Remote Similarity	NPD7503	Approved
0.6833	Remote Similarity	NPD4697	Phase 3
0.6825	Remote Similarity	NPD5128	Approved
0.6807	Remote Similarity	NPD7748	Approved
0.6803	Remote Similarity	NPD7640	Approved
0.6803	Remote Similarity	NPD7639	Approved
0.6752	Remote Similarity	NPD4753	Phase 2
0.6752	Remote Similarity	NPD5328	Approved
0.6723	Remote Similarity	NPD4202	Approved
0.6694	Remote Similarity	NPD5221	Approved
0.6694	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD5173	Approved
0.6639	Remote Similarity	NPD6079	Approved
0.6639	Remote Similarity	NPD7515	Phase 2
0.6638	Remote Similarity	NPD6098	Approved
0.6618	Remote Similarity	NPD6067	Discontinued
0.6614	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4629	Approved
0.6612	Remote Similarity	NPD5210	Approved
0.661	Remote Similarity	NPD6080	Approved
0.661	Remote Similarity	NPD6904	Approved
0.661	Remote Similarity	NPD6673	Approved
0.6609	Remote Similarity	NPD4786	Approved
0.6593	Remote Similarity	NPD8515	Approved
0.6593	Remote Similarity	NPD8513	Phase 3
0.6593	Remote Similarity	NPD8516	Approved
0.6593	Remote Similarity	NPD8517	Approved
0.6591	Remote Similarity	NPD6868	Approved
0.6589	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5169	Approved
0.6589	Remote Similarity	NPD5135	Approved
0.6552	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5127	Approved
0.6525	Remote Similarity	NPD6903	Approved
0.6525	Remote Similarity	NPD6672	Approved
0.6525	Remote Similarity	NPD5737	Approved
0.6496	Remote Similarity	NPD6409	Approved
0.6496	Remote Similarity	NPD3618	Phase 1
0.6496	Remote Similarity	NPD7334	Approved
0.6496	Remote Similarity	NPD5330	Approved
0.6496	Remote Similarity	NPD7146	Approved
0.6496	Remote Similarity	NPD6684	Approved
0.6496	Remote Similarity	NPD7521	Approved
0.6479	Remote Similarity	NPD6845	Suspended
0.6454	Remote Similarity	NPD5956	Approved
0.6435	Remote Similarity	NPD3667	Approved
0.6434	Remote Similarity	NPD6686	Approved
0.6429	Remote Similarity	NPD7632	Discontinued
0.6412	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5329	Approved
0.6408	Remote Similarity	NPD7260	Phase 2
0.6393	Remote Similarity	NPD5282	Discontinued
0.6391	Remote Similarity	NPD5167	Approved
0.6372	Remote Similarity	NPD6118	Approved
0.6372	Remote Similarity	NPD6114	Approved
0.6372	Remote Similarity	NPD6697	Approved
0.6372	Remote Similarity	NPD6115	Approved
0.637	Remote Similarity	NPD6334	Approved
0.637	Remote Similarity	NPD6333	Approved
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5693	Phase 1
0.6349	Remote Similarity	NPD4159	Approved
0.6349	Remote Similarity	NPD5344	Discontinued
0.6336	Remote Similarity	NPD6371	Approved
0.6333	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3665	Phase 1
0.6325	Remote Similarity	NPD3133	Approved
0.6325	Remote Similarity	NPD3666	Approved
0.6325	Remote Similarity	NPD4197	Approved
0.632	Remote Similarity	NPD4225	Approved
0.6311	Remote Similarity	NPD8171	Discontinued
0.6303	Remote Similarity	NPD7524	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