NPASS Compound

Structure

CID267822 OpenBabel06191716072D 53 59 0 0 1 0 0 0 0 0999 V2000 9.4496 1.2910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5977 2.7655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5179 1.7991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1915 2.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6379 -4.6119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1641 -3.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4882 0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0444 -0.6516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3498 -0.6264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7570 -0.6828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7466 1.2905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7841 1.7793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1923 -0.1851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8964 -3.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5980 1.7823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6355 1.2887 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1917 1.7823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4896 -4.1198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0399 -2.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1926 -1.1682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7476 -2.6430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3402 0.3065 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9335 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7469 0.3073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3408 -1.6603 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6364 0.3060 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4887 -1.1687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7858 -0.1861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7473 -1.6593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3411 -2.6440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7861 -1.1692 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1932 -3.1356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8959 -1.1677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5783 0.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4885 -0.1856 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0447 -1.6598 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9343 0.3045 0.0000 C 0 0 2 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 6.0450 -2.6435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0438 1.2907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3417 -4.6114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8646 -3.3815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5985 -0.1841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1934 -4.1379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5977 0.7936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2128 -0.9969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0452 -3.6435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3400 1.2902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4893 -3.1361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0911 -1.8646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5994 -2.1509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0014 1.5900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8956 -0.1845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 35 1 0 0 0 0 8 36 1 0 0 0 0 9 37 1 0 0 0 0 10 38 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 23 2 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 39 1 0 0 0 0 16 3 1 1 0 0 0 16 26 1 0 0 0 0 17 40 2 0 0 0 0 17 48 1 0 0 0 0 18 41 2 0 0 0 0 18 49 1 0 0 0 0 19 42 2 0 0 0 0 19 50 1 0 0 0 0 20 25 1 0 0 0 0 20 36 1 6 0 0 0 21 14 1 1 0 0 0 21 29 1 0 0 0 0 21 51 1 0 0 0 0 22 35 1 1 0 0 0 22 48 1 0 0 0 0 23 37 1 0 0 0 0 23 52 1 0 0 0 0 24 43 2 0 0 0 0 24 53 1 0 0 0 0 25 27 1 0 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 35 1 0 0 0 0 27 31 1 0 0 0 0 27 35 1 0 0 0 0 28 31 1 0 0 0 0 28 37 1 0 0 0 0 29 33 1 0 0 0 0 29 51 1 0 0 0 0 30 32 1 0 0 0 0 30 49 1 0 0 0 0 31 50 1 0 0 0 0 32 39 1 0 0 0 0 32 44 2 0 0 0 0 33 36 1 0 0 0 0 33 53 1 0 0 0 0 34 38 1 0 0 0 0 34 45 2 0 0 0 0 34 52 1 0 0 0 0 36 39 1 0 0 0 0 37 38 1 0 0 0 0 38 46 1 0 0 0 0 39 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	744.34
Volume:	727.813
LogP:	3.693
LogD:	2.904
LogS:	-4.369
# Rotatable Bonds:	10
TPSA:	201.56
# H-Bond Aceptor:	14
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	6.402
Fsp3:	0.795
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:	-5.277
MDCK Permeability:	0.00037534485454671085
Pgp-inhibitor:	1.0
Pgp-substrate:	0.417
Human Intestinal Absorption (HIA):	0.559
20% Bioavailability (F20%):	0.061
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	39.517799377441406%
Volume Distribution (VD):	0.694
Pgp-substrate:	27.36552619934082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.138
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.409
CYP3A4-substrate:	0.571

ADMET: Excretion

Clearance (CL):	3.848
Half-life (T1/2):	0.618

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.548
Drug-inuced Liver Injury (DILI):	0.763
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.803
Maximum Recommended Daily Dose:	0.698
Skin Sensitization:	0.399
Carcinogencity:	0.422
Eye Corrosion:	0.28
Eye Irritation:	0.017
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC267822

Natural Product ID:	NPC267822
*Common Name:**	Taccalonolide T
IUPAC Name:	n.a.
Synonyms:	Taccalonolide T
Standard InCHIKey:	KZLSRGBNLVIVQO-PKZSBVJESA-N
Standard InCHI:	InChI=1S/C39H52O14/c1-15(2)11-24(43)53-33-29-21(51-29)14-39(47)32(44)30(49-18(5)41)25-20(36(33,39)8)13-22(48-17(4)40)35(7)26-16(3)12-23-37(9,38(10,46)34(45)52-23)28(26)31(27(25)35)50-19(6)42/h12,15-16,20-22,25-31,33,46-47H,11,13-14H2,1-10H3/t16-,20+,21+,22+,25-,26+,27-,28+,29+,30-,31-,33+,35-,36+,37+,38-,39+/m1/s1
SMILES:	CC(CC(=O)O[C@H]1[C@H]2O[C@H]2C[C@]2([C@@]1(C)[C@H]1C[C@H](OC(=O)C)[C@]3([C@H]([C@@H]1[C@H](C2=O)OC(=O)C)[C@@H](OC(=O)C)[C@@H]1[C@@H]3[C@H](C)C=C2[C@]1(C)[C@](C)(O)C(=O)O2)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821843
PubChem CID:	56658581
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	=	335.0	nM	PMID[525057]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	335.0	nM	PMID[525058]

☑ 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 NPC267822 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	312
0.1-0.2	1955
0.2-0.3	5749
0.3-0.4	10394
0.4-0.5	11164
0.5-0.6	6312
0.6-0.7	5260
0.7-0.8	1467
0.8-0.85	71
0.85-0.9	8
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC169818
0.9825	High Similarity	NPC43252
0.9825	High Similarity	NPC135038
0.9737	High Similarity	NPC65858
0.8621	High Similarity	NPC280782
0.8595	High Similarity	NPC222688
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
0.8319	Intermediate Similarity	NPC473798
0.8306	Intermediate Similarity	NPC473255
0.8305	Intermediate Similarity	NPC90769
0.8279	Intermediate Similarity	NPC471406
0.8276	Intermediate Similarity	NPC94529
0.8261	Intermediate Similarity	NPC475571
0.825	Intermediate Similarity	NPC474734
0.8235	Intermediate Similarity	NPC202889
0.8235	Intermediate Similarity	NPC49451
0.8211	Intermediate Similarity	NPC477046
0.8211	Intermediate Similarity	NPC102822
0.8203	Intermediate Similarity	NPC473519
0.8203	Intermediate Similarity	NPC473805
0.8197	Intermediate Similarity	NPC470777
0.8197	Intermediate Similarity	NPC473203
0.819	Intermediate Similarity	NPC59530
0.8189	Intermediate Similarity	NPC231529
0.8189	Intermediate Similarity	NPC470880
0.8182	Intermediate Similarity	NPC474654
0.8182	Intermediate Similarity	NPC470854
0.8182	Intermediate Similarity	NPC287343
0.8182	Intermediate Similarity	NPC97908
0.8182	Intermediate Similarity	NPC473590
0.8182	Intermediate Similarity	NPC122033
0.8175	Intermediate Similarity	NPC470882
0.8175	Intermediate Similarity	NPC473253
0.816	Intermediate Similarity	NPC475194
0.814	Intermediate Similarity	NPC102015
0.813	Intermediate Similarity	NPC109973
0.812	Intermediate Similarity	NPC258323
0.8115	Intermediate Similarity	NPC17772
0.8115	Intermediate Similarity	NPC118638
0.811	Intermediate Similarity	NPC69273
0.811	Intermediate Similarity	NPC293623
0.811	Intermediate Similarity	NPC168899
0.8103	Intermediate Similarity	NPC196528
0.8103	Intermediate Similarity	NPC278628
0.8103	Intermediate Similarity	NPC231530
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	NPC179626
0.8099	Intermediate Similarity	NPC152199
0.8099	Intermediate Similarity	NPC49492
0.8099	Intermediate Similarity	NPC266728
0.8095	Intermediate Similarity	NPC473635
0.8083	Intermediate Similarity	NPC194100
0.8083	Intermediate Similarity	NPC477266
0.8083	Intermediate Similarity	NPC198539
0.8083	Intermediate Similarity	NPC97002
0.808	Intermediate Similarity	NPC227397
0.8067	Intermediate Similarity	NPC43775
0.8065	Intermediate Similarity	NPC310511
0.8051	Intermediate Similarity	NPC27814
0.8033	Intermediate Similarity	NPC176513
0.8033	Intermediate Similarity	NPC470775
0.8031	Intermediate Similarity	NPC473265
0.8017	Intermediate Similarity	NPC323821
0.8017	Intermediate Similarity	NPC143268
0.8017	Intermediate Similarity	NPC45218
0.8017	Intermediate Similarity	NPC29705
0.8017	Intermediate Similarity	NPC18547
0.8017	Intermediate Similarity	NPC268238
0.8017	Intermediate Similarity	NPC471293
0.8017	Intermediate Similarity	NPC474906
0.8016	Intermediate Similarity	NPC469790
0.8015	Intermediate Similarity	NPC256618
0.8015	Intermediate Similarity	NPC219058
0.8	Intermediate Similarity	NPC474516
0.7984	Intermediate Similarity	NPC473838
0.7984	Intermediate Similarity	NPC251226
0.7984	Intermediate Similarity	NPC475389
0.7984	Intermediate Similarity	NPC241008
0.7967	Intermediate Similarity	NPC470776
0.7967	Intermediate Similarity	NPC188667
0.7967	Intermediate Similarity	NPC297179
0.7967	Intermediate Similarity	NPC204552
0.7953	Intermediate Similarity	NPC47113
0.7953	Intermediate Similarity	NPC174367
0.7951	Intermediate Similarity	NPC259306
0.7951	Intermediate Similarity	NPC207217
0.7951	Intermediate Similarity	NPC470628
0.7951	Intermediate Similarity	NPC474046
0.7939	Intermediate Similarity	NPC475376
0.7937	Intermediate Similarity	NPC91693
0.7937	Intermediate Similarity	NPC473979
0.7937	Intermediate Similarity	NPC265557
0.7937	Intermediate Similarity	NPC18945
0.7937	Intermediate Similarity	NPC105926
0.7934	Intermediate Similarity	NPC73300
0.7934	Intermediate Similarity	NPC52634
0.7934	Intermediate Similarity	NPC250109
0.7934	Intermediate Similarity	NPC108721
0.7934	Intermediate Similarity	NPC7921
0.7934	Intermediate Similarity	NPC208998
0.7934	Intermediate Similarity	NPC962
0.7934	Intermediate Similarity	NPC317210
0.7931	Intermediate Similarity	NPC140723
0.7931	Intermediate Similarity	NPC191892
0.7923	Intermediate Similarity	NPC471855
0.792	Intermediate Similarity	NPC159456
0.792	Intermediate Similarity	NPC275675
0.792	Intermediate Similarity	NPC4021
0.7917	Intermediate Similarity	NPC472003
0.7907	Intermediate Similarity	NPC54614
0.7907	Intermediate Similarity	NPC309096
0.7903	Intermediate Similarity	NPC475041
0.7903	Intermediate Similarity	NPC469488
0.7903	Intermediate Similarity	NPC42673
0.7891	Intermediate Similarity	NPC305496
0.7886	Intermediate Similarity	NPC471854
0.7881	Intermediate Similarity	NPC144854
0.7881	Intermediate Similarity	NPC3316
0.7881	Intermediate Similarity	NPC165873
0.7874	Intermediate Similarity	NPC476729
0.7874	Intermediate Similarity	NPC24651
0.7869	Intermediate Similarity	NPC326542
0.7869	Intermediate Similarity	NPC469877
0.7869	Intermediate Similarity	NPC470919
0.7863	Intermediate Similarity	NPC65523
0.7863	Intermediate Similarity	NPC328737
0.7857	Intermediate Similarity	NPC312833
0.7857	Intermediate Similarity	NPC170538
0.7857	Intermediate Similarity	NPC269642
0.7851	Intermediate Similarity	NPC11252
0.7851	Intermediate Similarity	NPC207251
0.7851	Intermediate Similarity	NPC170487
0.7851	Intermediate Similarity	NPC289312
0.7851	Intermediate Similarity	NPC71348
0.7851	Intermediate Similarity	NPC472002
0.7845	Intermediate Similarity	NPC473928
0.7845	Intermediate Similarity	NPC477054
0.784	Intermediate Similarity	NPC143755
0.784	Intermediate Similarity	NPC268530
0.784	Intermediate Similarity	NPC478051
0.784	Intermediate Similarity	NPC154491
0.784	Intermediate Similarity	NPC112038
0.784	Intermediate Similarity	NPC241192
0.7836	Intermediate Similarity	NPC290746
0.7836	Intermediate Similarity	NPC79250
0.7833	Intermediate Similarity	NPC5284
0.7829	Intermediate Similarity	NPC475636
0.7829	Intermediate Similarity	NPC295220
0.7829	Intermediate Similarity	NPC476091
0.7829	Intermediate Similarity	NPC188291
0.7829	Intermediate Similarity	NPC476078
0.7823	Intermediate Similarity	NPC257457
0.7823	Intermediate Similarity	NPC311554
0.7823	Intermediate Similarity	NPC251310
0.7815	Intermediate Similarity	NPC192813
0.7815	Intermediate Similarity	NPC277017
0.7815	Intermediate Similarity	NPC154608
0.7815	Intermediate Similarity	NPC293850
0.7812	Intermediate Similarity	NPC293112
0.7812	Intermediate Similarity	NPC93368
0.7812	Intermediate Similarity	NPC477745
0.7805	Intermediate Similarity	NPC298278
0.7797	Intermediate Similarity	NPC50535
0.7797	Intermediate Similarity	NPC472655
0.7797	Intermediate Similarity	NPC477877
0.7797	Intermediate Similarity	NPC470587
0.7795	Intermediate Similarity	NPC120724
0.7795	Intermediate Similarity	NPC67251
0.7795	Intermediate Similarity	NPC11895
0.7786	Intermediate Similarity	NPC6274
0.7786	Intermediate Similarity	NPC42206
0.7786	Intermediate Similarity	NPC254146
0.7786	Intermediate Similarity	NPC33378
0.7778	Intermediate Similarity	NPC470779
0.7778	Intermediate Similarity	NPC42675
0.7778	Intermediate Similarity	NPC470921
0.7769	Intermediate Similarity	NPC201992
0.7769	Intermediate Similarity	NPC146945
0.7769	Intermediate Similarity	NPC471407
0.7769	Intermediate Similarity	NPC214797
0.7769	Intermediate Similarity	NPC118860
0.7769	Intermediate Similarity	NPC171888
0.7769	Intermediate Similarity	NPC470281
0.7769	Intermediate Similarity	NPC231589
0.7769	Intermediate Similarity	NPC221414
0.776	Intermediate Similarity	NPC230513
0.776	Intermediate Similarity	NPC161738
0.776	Intermediate Similarity	NPC61520
0.776	Intermediate Similarity	NPC161065
0.776	Intermediate Similarity	NPC473920
0.776	Intermediate Similarity	NPC127530
0.776	Intermediate Similarity	NPC472667

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 NPC267822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	2216
0.2-0.3	4030
0.3-0.4	1683
0.4-0.5	513
0.5-0.6	227
0.6-0.7	152
0.7-0.8	55
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
0.7769	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	NPD6054	Approved
0.7698	Intermediate Similarity	NPD6059	Approved
0.7674	Intermediate Similarity	NPD6616	Approved
0.7667	Intermediate Similarity	NPD6881	Approved
0.7667	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD4632	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
0.7521	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD6015	Approved
0.75	Intermediate Similarity	NPD6016	Approved
0.748	Intermediate Similarity	NPD6847	Approved
0.748	Intermediate Similarity	NPD6617	Approved
0.748	Intermediate Similarity	NPD6869	Approved
0.746	Intermediate Similarity	NPD6009	Approved
0.746	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6014	Approved
0.7459	Intermediate Similarity	NPD6013	Approved
0.7459	Intermediate Similarity	NPD6012	Approved
0.7458	Intermediate Similarity	NPD1700	Approved
0.7442	Intermediate Similarity	NPD5988	Approved
0.7405	Intermediate Similarity	NPD7507	Approved
0.7385	Intermediate Similarity	NPD8328	Phase 3
0.7377	Intermediate Similarity	NPD6011	Approved
0.7368	Intermediate Similarity	NPD7319	Approved
0.7364	Intermediate Similarity	NPD5983	Phase 2
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6336	Discontinued
0.7258	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7516	Approved
0.7203	Intermediate Similarity	NPD4755	Approved
0.7203	Intermediate Similarity	NPD6084	Phase 2
0.7203	Intermediate Similarity	NPD6083	Phase 2
0.7188	Intermediate Similarity	NPD7115	Discovery
0.7177	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6033	Approved
0.7155	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD5696	Approved
0.7132	Intermediate Similarity	NPD7327	Approved
0.7132	Intermediate Similarity	NPD7328	Approved
0.712	Intermediate Similarity	NPD4634	Approved
0.7109	Intermediate Similarity	NPD6274	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7077	Intermediate Similarity	NPD7101	Approved
0.7077	Intermediate Similarity	NPD7100	Approved
0.7034	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5695	Phase 3
0.7016	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD6335	Approved
0.6992	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8335	Approved
0.697	Remote Similarity	NPD8379	Approved
0.697	Remote Similarity	NPD8378	Approved
0.697	Remote Similarity	NPD6909	Approved
0.697	Remote Similarity	NPD6908	Approved
0.697	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8296	Approved
0.697	Remote Similarity	NPD8033	Approved
0.697	Remote Similarity	NPD6921	Approved
0.697	Remote Similarity	NPD8380	Approved
0.6967	Remote Similarity	NPD5226	Approved
0.6967	Remote Similarity	NPD4633	Approved
0.6967	Remote Similarity	NPD5224	Approved
0.6967	Remote Similarity	NPD5225	Approved
0.6967	Remote Similarity	NPD5211	Phase 2
0.6935	Remote Similarity	NPD4767	Approved
0.6935	Remote Similarity	NPD4768	Approved
0.6923	Remote Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD8034	Phase 2
0.6923	Remote Similarity	NPD6317	Approved
0.6917	Remote Similarity	NPD7902	Approved
0.6911	Remote Similarity	NPD5175	Approved
0.6911	Remote Similarity	NPD5174	Approved
0.6894	Remote Similarity	NPD8377	Approved
0.6894	Remote Similarity	NPD8294	Approved
0.6885	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD6053	Discontinued
0.687	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD6314	Approved
0.6855	Remote Similarity	NPD5141	Approved
0.6825	Remote Similarity	NPD4730	Approved
0.6825	Remote Similarity	NPD4729	Approved
0.6822	Remote Similarity	NPD8133	Approved
0.6807	Remote Similarity	NPD7748	Approved
0.6783	Remote Similarity	NPD6098	Approved
0.6774	Remote Similarity	NPD4754	Approved
0.6752	Remote Similarity	NPD6673	Approved
0.6752	Remote Similarity	NPD6904	Approved
0.6752	Remote Similarity	NPD6080	Approved
0.6721	Remote Similarity	NPD7638	Approved
0.6719	Remote Similarity	NPD5251	Approved
0.6719	Remote Similarity	NPD5248	Approved
0.6719	Remote Similarity	NPD5250	Approved
0.6719	Remote Similarity	NPD5249	Phase 3
0.6719	Remote Similarity	NPD5247	Approved
0.6716	Remote Similarity	NPD7503	Approved
0.6694	Remote Similarity	NPD4697	Phase 3
0.6693	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6614	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5328	Approved
0.661	Remote Similarity	NPD4753	Phase 2
0.6591	Remote Similarity	NPD6868	Approved
0.6583	Remote Similarity	NPD4202	Approved
0.6557	Remote Similarity	NPD5222	Approved
0.6557	Remote Similarity	NPD5221	Approved
0.6557	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5215	Approved
0.6538	Remote Similarity	NPD5216	Approved
0.6538	Remote Similarity	NPD5217	Approved
0.6525	Remote Similarity	NPD6903	Approved
0.6504	Remote Similarity	NPD5173	Approved
0.65	Remote Similarity	NPD5693	Phase 1
0.65	Remote Similarity	NPD6079	Approved
0.65	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD6050	Approved
0.6496	Remote Similarity	NPD6409	Approved
0.6496	Remote Similarity	NPD7521	Approved
0.6496	Remote Similarity	NPD6067	Discontinued
0.6496	Remote Similarity	NPD7334	Approved
0.6496	Remote Similarity	NPD5330	Approved
0.6496	Remote Similarity	NPD7146	Approved
0.6496	Remote Similarity	NPD6684	Approved
0.6479	Remote Similarity	NPD6845	Suspended
0.6475	Remote Similarity	NPD5210	Approved
0.6475	Remote Similarity	NPD4629	Approved
0.6471	Remote Similarity	NPD8513	Phase 3
0.6471	Remote Similarity	NPD8516	Approved
0.6471	Remote Similarity	NPD8517	Approved
0.6471	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD4786	Approved
0.6462	Remote Similarity	NPD5169	Approved
0.6462	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5135	Approved
0.6454	Remote Similarity	NPD5956	Approved
0.6417	Remote Similarity	NPD5692	Phase 3
0.6412	Remote Similarity	NPD5127	Approved
0.641	Remote Similarity	NPD5329	Approved
0.641	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7260	Phase 2
0.6393	Remote Similarity	NPD5282	Discontinued
0.637	Remote Similarity	NPD6334	Approved
0.637	Remote Similarity	NPD6333	Approved
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6356	Remote Similarity	NPD3618	Phase 1
0.6333	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4197	Approved
0.6308	Remote Similarity	NPD6686	Approved
0.6299	Remote Similarity	NPD7632	Discontinued
0.6293	Remote Similarity	NPD3667	Approved
0.6288	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5207	Approved
0.6269	Remote Similarity	NPD5167	Approved
0.6265	Remote Similarity	NPD7799	Discontinued
0.624	Remote Similarity	NPD5959	Approved
0.6228	Remote Similarity	NPD6114	Approved
0.6228	Remote Similarity	NPD6115	Approved
0.6228	Remote Similarity	NPD6697	Approved
0.6228	Remote Similarity	NPD6118	Approved
0.622	Remote Similarity	NPD5344	Discontinued
0.622	Remote Similarity	NPD4159	Approved
0.6218	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6371	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